Preparation of N,N-Dimethyl Aromatic Amides from Aromatic
Aldehydes with Dimethylamine and Iodine Reagents

Haruka Baba; Katsuhiko Moriyama; Hideo Togo

doi:10.1055/s-0031-1290659

LETTER

Preparation of N,N-Dimethyl Aromatic Amides from Aromatic Aldehydes with Dimethylamine and Iodine Reagents

Haruka Baba, Katsuhiko Moriyama, Hideo Togo*
Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
e-Mail: togo@faculty.chiba-u.jp;

Abstract

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Abstract

Various N,N-dimethyl aromatic amides were obtained in good to moderate yields by the reaction of aromatic aldehydes with aqueous dimethylamine in the presence of molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) at room temperature. Under the same conditions and using the same procedure, treatment of aromatic aldehydes and morpholine in the presence of DIH also provided the corresponding N-aroyl morpholines in good to moderate yields.

Key words

amides - aldehydes - amines - iodine - synthetic methods

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References

References and Notes

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Preparation of N , N -Dimethyl-4-bromobenzamide; Typical Procedure: 4-Bromobenzaldehyde (1.0 mmol, 185 mg), aq dimethylamine (50%, 3.0 mmol, 0.32 mL), 1,3-diiodo-5,5-dimethylhydantoin (1.0 mmol, 380 mg), and K₂CO₃ (1.0 mmol, 138 mg) were added to CCl₄ (3 mL).
The mixture was stirred at r.t. for 24 h under an argon atmosphere. Upon completion, the mixture was poured into sat. aq sodium sulfite solution and extracted with chloroform (3 × 20 mL). The organic layer was dried over Na₂SO₄. After filtration and removal of the solvent under reduced pressure, the residue was subjected to short column chromatography on silica gel (hexane/ethyl acetate, 3:2) to give N,N-dimethyl-
4-bromobenzamide in 72% yield.
Mp 73 ˚C (Lit.⁸ 76-79 ˚C); IR (neat): 1626 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.97 (s, 3 H), 3.10 (s, 3 H), 7.30 (d, J = 8.6 Hz, 2 H), 7.54 (d, J = 8.6 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.4, 39.5, 123.8, 128.8, 131.6, 135.1, 170.5; HRMS (ESI): m/z [M + H]⁺ calcd for C₉H₁₁ONBr: 228.0019; found: 228.0021.
N , N -Dimethyl- p -chlorobenzamide: Oil; IR (neat): 1640 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.97 (s, 3 H), 3.10 (s, 3 H), 7.37 (br s, 4 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.2, 39.4, 128.1, 128.5, 134.5, 135.4, 170.3; HRMS (ESI): m/z [M + H]⁺ calcd for C₉H₁₁ONCl: 184.0524; found: 184.0526.
N , N -Dimethyl- p -fluorobenzamide: Oil (Lit.⁹ mp 64 ˚C); IR (neat): 1633 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.99 (s, 3 H), 3.10 (s, 3 H), 7.10 (t, J = 8.8 Hz, 2 H), 7.43 (dd, J = 8.8, 5.5 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.4, 39.5, 115.3 (J = 21.9 Hz), 129.2 (J = 8.6 Hz), 132.2, 163.2 (J = 249.9 Hz), 170.6; HRMS (ESI): m/z [M + H]⁺ calcd for C₉H₁₁ONF: 168.0819; found: 168.0821.
N , N -Dimethyl- p -nitrobenzamide: Mp 89-93 ˚C (Lit.⁸
99-103 ˚C); IR (Nujol): 1377, 1514, 1643 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.98 (s, 3 H), 3.15 (s, 3 H), 7.60 (d, J = 7.3 Hz, 2 H), 8.28 (d, J = 7.3 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.3, 39.3, 123.7, 128.0, 142.4, 148.2, 169.2; HRMS (ESI): m/z [M + H]⁺ calcd for C₉H₁₁O₃N₂: 195.0764; found: 195.0768.
N , N -Dimethyl- m -nitrobenzamide: Mp 76-77 ˚C (Lit.^¹0 81 ˚C); IR (Nujol): 1377, 1533, 1635 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.01 (s, 3 H), 3.15 (s, 3 H), 7.61 (td, J = 7.7, 1.0 Hz, 1 H), 7.77 (dt, J = 7.7, 1.4 Hz, 1 H), 8.27-8.30 (m, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.5, 39.5, 122.2, 124.3, 129.7, 133.1, 137.8, 147.9, 168.9; HRMS (ESI): m/z [M + H]⁺ calcd for C₉H₁₁O₃N₂: 195.0764; found: 195.0768.
N , N -Dimethyl- p -cyanobenzamide: Oil (Lit.⁸ mp 100-105 ˚C); IR (neat): 1631, 2230 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.96 (s, 3 H), 3.13 (s, 3 H), 7.52 (d, J = 8.2 Hz, 2 H), 7.71 (d, J = 8.2 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS):
δ = 35.2, 39.2, 113.2, 118.0, 127.6, 132.2, 140.5, 169.4; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₀H₁₁ON₂: 175.0866; found: 175.0869.

N , N -Dimethyl- p -(trifluoromethyl)benzamide: Mp 75 ˚C (Lit.⁹ 65-75 ˚C); IR (Nujol): 1337, 1625 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.97 (s, 3 H), 3.13 (s, 3 H), 7.53 (d, J = 7.9 Hz, 2 H), 7.68 (d, J = 7.9 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.2, 39.3, 123.7 (J _C-F = 272.8 Hz), 125.5, 127.4, 131.4 (J _C-F = 32.4 Hz), 140.0, 170.2; HRMS (ESI): m/z
[M + H]⁺ calcd for C₁₀H₁₁ONF₃: 218.0787; found: 218.0788.
N , N -Dimethylbenzamide: Oil (commercial); IR (neat): 1625 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.98 (s, 3 H), 3.12 (s, 3 H), 7.41 (br s, 5 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.3, 39.5, 126.9, 128.3, 129.4, 136.2, 171.6.
N , N -Diimethyl- p -methylbenzamide: Oil; IR (neat): 1625 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.37 (s, 3 H), 2.99 (s, 3 H), 3.10 (s, 3 H), 7.19 (d, J = 7.9 Hz, 2 H), 7.31 (d, J = 7.9 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 21.3, 35.4, 39.6, 137.2, 128.9, 133.4, 139.6, 171.8; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₀H₁₄ON: 164.1070; found: 164.1071.
N , N -Dimethyl- p -methoxybenzamide: Oil; IR (neat): 1252, 1610 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.06 (s, 6 H), 3.83 (s, 3 H), 6.90 (d, J = 8.8 Hz, 2 H), 7.40 (d, J = 8.8 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.5, 39.7, 55.2, 113.4, 128.2, 129.0, 160.5, 171.5; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₀H₁₄ O₂N: 180.1019,; found: 180.1021.
N , N -Dimethyl-1-naphthalenecarboxamide: Oil (Lit.^¹¹
mp 61-62 ˚C); IR (neat): 1615 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.82 (s, 3 H), 3.26 (s, 3 H), 7.42 (dd, J = 7.1, 1.2 Hz, 1 H), 7.46-7.54 (m, 3 H), 7.78-7.80 (m, 1 H), 7.84-7.88 (m, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 34.8, 38.8, 123.8, 124.8, 125.1, 126.3, 126.9, 128.3, 128.9, 129.4, 133.4, 134.7, 170.8; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₃H₁₄ON: 200.1070; found: 200.1070.
N , N -Dimethyl-2-thiophenecarboxamide: Oil; IR (neat): 1619 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.19 (s, 6 H), 7.05 (dd, J = 5.0, 3.7 Hz, 1 H), 7.36 (dd, J = 3.7, 1.2 Hz, 1 H), 7.45 (dd, J = 5.0, 1.2 Hz, 1 H); ^¹³C NMR (CDCl₃, TMS):
δ = 35.2, 39.2, 126.6, 128.7, 129.1, 137.8, 164.4; HRMS (ESI): m/z [M + Na]⁺ calcd for C₇H₉ONNaS: 178.0297; found: 178.0299.
N , N -Dimethyl-3-pyridinecarboxamide: Oil; IR (neat): 1633 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.02 (s, 3 H), 3.14 (s, 3 H), 7.36 (ddd, J = 7.8, 4.8, 0.9 Hz, 1 H), 7.77 (dt, J = 7.8, 2.0 Hz, 1 H), 8.66 (dd, J = 4.8, 2.0 Hz, 1 H), 8.69 (dd,
J = 2.0, 0.9 Hz, 1 H); ^¹³C NMR (CDCl₃, TMS): δ = 35.4, 39.5, 123.3, 132.0, 134.9, 147.9, 150.5, 168.9; HRMS (ESI): m/z [M + H]⁺ calcd for C₈H₁₁ON₂: 151.0866; found: 151.0867.
N , N -Dimethyl-1-benzothiophene-2-carboxamide: Mp 105 ˚C; IR (Nujol): 1615 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.22 (s, 6 H), 7.38-7.41 (m, 2 H), 7.53 (s, 1 H), 7.80-7.84 (m, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 36.2, 39.0, 122.3, 124.6, 124.6, 125.4, 125.7, 137.5, 138.7, 140.2, 164.8; HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₁H₁₁ONNaS: 228.0454; found: 228.0454.
N , N -Dimethylbenzofuran-2-carboxamide: Mp 71-73 ˚C; IR (Nujol): 1642 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.16 (s, 3 H), 3.36 (s, 3 H), 7.26-7.31 (m, 2 H), 7.40 (t, J = 8.0 Hz, 1 H), 7.53 (d, J = 8.0 Hz, 1 H), 7.66 (d, J = 8.0 Hz, 1 H); ^¹³C NMR (CDCl₃, TMS): δ = 36.2, 38.1, 111.7, 111.8, 122.2, 123.5, 126.3, 127.0, 149.3, 154.6, 161.0; HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₁H₁₁O₂NNa: 212.0682; found: 212.0682.
N , N , N -Trimethyl-1 H -indol-2-carboxamide: Oil; IR (neat): 1630 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.19 (s, 6 H), 3.85 (s, 3 H), 6.64 (s, 1 H), 7.14 (t, J = 8.1 Hz, 1 H), 7.29
(t, J = 8.1 Hz, 1 H), 7.36 (d, J = 8.1 Hz, 1 H), 7.63 (d, J = 8.1 Hz, 1 H); ^¹³C NMR (CDCl₃, TMS): δ = 31.0, 35.1, 39.5, 103.9, 109.7, 120.0, 121.4, 123.2, 126.3, 131.9, 137.7, 164.3; HRMS (ESI): m/z [M + Na]⁺ calcd for C₁₂H₁₄ON₂Na: 225.0998; found: 225.0999.
N -( p -Bromobenzoyl)morpholine: Oil; IR (neat): 1114, 1623 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.32-3.98 (m, 8 H), 7.29 (d, J = 8.3 Hz, 2 H), 7.56 (d, J = 8.3 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.7, 48.5, 66.7, 124.2, 128.8, 131.8, 134.0, 169.3; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₁H₁₃O₂NBr: 270.0124; found: 270.0127.
N -( p -Chlorobenzoyl)morpholine: Mp 69-70 ˚C (Lit.^¹²
76-77 ˚C); IR (Nujol): 1110, 1627 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.36-3.98 (m, 8 H), 7.36 (d, J = 8.7 Hz, 2 H), 7.40 (d, J = 8.7 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.9, 48.0, 66.8, 128.6, 128.8, 133.6, 136.0, 169.3; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₁H₁₃O₂NCl: 226.0629; found: 226.0628.
N -( p -Fluorobenzoyl)morpholine: Oil; IR (neat): 1115, 1636 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.84-3.99 (m, 8 H), 7.11 (t, J = 8.8 Hz, 2 H), 7.43 (dd, J = 8.8, 5.5 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.7, 48.2, 66.8, 115.7 (J = 21.9 Hz), 129.4 (J = 8.6 Hz), 131.3, 163.5 (J = 249.9 Hz), 169.4; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₁H₁₃O₂NF: 210.0925; found: 210.0920.
N -( p -Nitrobenzoyl)morpholine: Mp 97-99 ˚C; IR (Nujol): 1107, 1350, 1509, 1622 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.29-3.95 (m, 8 H), 7.59 (d, J = 8.8 Hz, 2 H), 8.29 (d, J = 8.8 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.5, 48.0, 66.7, 123.9, 128.1, 141.4, 148.4, 168.0; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₁H₁₃N₂O₄: 237.0870; found: 237.0873.
N -( m -Nitrobenzoyl)morpholine: Mp 86-87 ˚C (Lit.^¹³ 87-88 ˚C); IR (neat): 1115, 1354, 1535, 1650 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.38-3.95 (m, 8 H), 7.64 (t, J = 7.8 Hz, 1 H), 7.76 (dt, J = 7.8, 1.3 Hz, 1 H), 8.27-8.32 (m, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.5, 48.1, 66.7, 122.3, 124.7, 129.9, 133.1, 136.9, 148.1, 167.7; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₂H₁₃O₄N₂: 237.0870; found: 237.0870.
N -( p -Cyanobenzoyl)morpholine: Mp 138 ˚C (Lit.^¹³ 141-142 ˚C); IR (Nujol): 1109, 1621, 2224 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.30-3.91 (m, 8 H), 7.52 (d, J = 8.5 Hz, 2 H), 7.73 (d, J = 8.5 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS):
δ = 42.5, 47.9, 66.6, 113.6, 117.9, 127.7, 132.4, 139.5, 168.2; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₂H₁₃O₂N₂: 217.0972; found: 217.0971.
N -( p -Trifluorobenzoyl)morpholine: Oil; IR (neat): 1112, 1326, 1633 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.30-3.98 (m, 8 H), 7.53 (d, J = 8.1 Hz, 2 H), 7.70 (d, J = 8.1 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.6, 48.1, 66.8, 123.6 (J _C-F = 272.7 Hz), 125.7, 127.4, 131.7 (J _C-F = 32.5 Hz), 138.9, 168.9; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₂H₁₃O₂NF₃: 260.0893; found: 260.0893.
N -( p -Methylbenzoyl)morpholine: Oil; IR (neat): 1115, 1631 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 2.38 (s, 3 H), 3.36-3.92 (m, 8 H), 7.21 (d, J = 8.2 Hz, 2 H), 7.31 (d, J = 8.2 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 21.3, 43.2, 48.3, 66.8, 127.1, 129.1, 132.2, 140.0, 170.6; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₂H₁₆O₂N: 206.1176; found: 206.1177.
N -( p -Methoxybenzoyl)morpholine: Oil; IR (neat): 1115, 1260, 1602 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.59-3.79 (m, 8 H), 3.84 (s, 3 H), 6.92 (d, J = 8.8 Hz, 2 H), 7.39 (d, J = 8.8 Hz, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 43.1, 48.7, 55.3, 66.8, 113.7, 127.2, 129.2, 160.8, 170.4; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₂H₁₆O₃N: 222.1125; found: 222.1125.
N -Benzoylmorpholine: Oil (Lit.^¹4 mp 72-73 ˚C); IR (neat): 1115, 1630 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.36-3.93 (m, 8 H), 7.38-7.52 (m, 5 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.2, 48.3, 66.9, 127.1, 128.5, 129.9, 135.3, 170.4; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₁H₁₄O₂N: 192.1019; found: 192.1014.
N -(1-Naphthalenylcarbonyl)morpholine: Oil; IR (neat): 1115, 1630 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.14-3.28 (m, 2 H), 3.46-3.59 (m, 2 H), 3.82-4.07 (m, 4 H), 7.41-7.58 (m, 4 H), 7.83-7.91 (m, 3 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.2, 47.6, 67.0, 123.9, 124.6, 125.1, 126.5, 127.1, 128.5, 129.3, 129.5, 133.4, 133.6, 169.5; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₅H₁₆O₂N: 242.1176; found: 242.1172.
N -(2-Thiophenylcarbonyl)morpholine: Oil; IR (neat): 1115, 1615 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.71-3.80
(m, 8 H), 7.05 (dd, J = 5.0, 3.6 Hz, 1 H), 7.29 (dd, J = 3.6, 1.1 Hz, 1 H), 7.46 (dd, J = 5.0 Hz, 1.1 Hz, 1 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.2, 47.6, 66.8, 126.7, 128.8, 128.9, 136.6, 163.6; HRMS (ESI): m/z [M + H]⁺ calcd for C₉H₁₂O₂NS: 198.0583; found: 198.0583.
N -(3-Pyridinylcarbonyl)morpholine: Oil; IR (neat): 1114, 1630 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.40-3.92 (m 8 H), 7.38 (ddd, J = 7.8, 4.8, 0.9 Hz, 1 H), 7.77 (dt, J = 8.0, 2.0 Hz, 1 H), 8.67-8.70 (m, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.3, 48.2, 66.8, 123.5, 131.1, 135.1, 148.0, 151.0, 167.8; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₀H₁₃O₂N₂: 193.0972; found: 193.0970.
N -(Benzothiophene-2-carbonyl)morpholine: Mp 90-92 ˚C; IR (Nujol): 1112, 1600 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.73-3.82 (m, 8 H), 7.38-7.44 (m, 2 H), 7.49 (s, 1 H), 7.79-7.88 (m, 2 H); ^¹³C NMR (CDCl₃, TMS): δ = 40.5, 40.5, 66.6, 122.2, 124.5, 124.7, 125.2, 125.7, 136.0, 138.4, 140.0, 163.7; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₃H₁₄O₂NS: 248.0740; found: 248.0737.
N -(Benzofuran-2-carbonyl)morpholine: Mp 92 ˚C;
IR (Nujol): 1108, 1609 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.76-3.82 (m, 4 H), 3.82-4.00 (m, 4 H), 7.30 (t, J = 7.7 Hz, 1 H), 7.35 (s, 1 H), 7.41 (t, J = 7.7 Hz, 1 H), 7.52 (d, J = 7.7 Hz, 1 H), 7.66 (d, J = 7.7 Hz, 1 H); ^¹³C NMR (CDCl₃, TMS): δ = 42.5, 46.5, 66.8, 111.7, 112.3, 122.2, 123.6, 126.5, 126.8, 148.7, 154.5, 159.6; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₃H₁₄O₃N: 232.0968; found: 232.0964.
N -( N -Methyl-1 H -indol-2-carbonyl)morpholine: Mp 109-112 ˚C; IR (Nujol): 1111, 1643 cm^-¹; ^¹H NMR (CDCl₃, TMS): δ = 3.71-3.84 (m, 8 H), 3.86 (s, 3 H), 6.60 (s, 1 H), 7.15 (t, J = 8.2 Hz, 1 H), 7.31 (t, J = 8.2 Hz, 1 H), 7.37 (d, J = 8.2 Hz, 1 H), 7.62 (d, J = 8.2 Hz, 1 H); ^¹³C NMR (CDCl₃, TMS): δ = 25.0, 31.1, 67.0, 103.9, 109.9, 120.4, 121.6, 123.5, 126.3, 131.1, 138.0, 163.2; HRMS (ESI): m/z [M + H]⁺ calcd for C₁₄H₁₇O₂N₂: 245.1285; found: 245.1278

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