Benzylamine → HCID 10694592, compound

HRID 1451854Notes

Reaction equation

HRID 1451854 reaction equation
[C:1]1(=[O:26])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:21])[C:3]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:2]12.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([NH:34][C:8](=[O:9])[CH2:7][CH:6]([N:5]1[C:1](=[O:26])[C:2]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:3]2[C:4]1=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 103608253-(3,4-Dimethoxyphenyl)-3-phthalimidopropanoic acid

Product 1

HCID 10694592HCID 10694592, compoundYield 92%

Procedure

The procedure of Example 46 is utilized starting with 3-phthalimido-3-(3,4'-dimethoxyphenyl)propionic acid and benzylamine (1.0 equiv) to afford 2.45 g (92%) of 3-phthalimido-3-(3',4'-dimethoxyphenyl)propionic benzylamide as white powder: mp 208.4°-209.8° C.; 1H NMR (DMSO-d6, 250 MHz) δ 8.60 (t, 1 H, J=6 Hz), 7.78-7.92 (m, 4 H), 6.85-7.20 (m, 8 H), 5.73 (t, 1 H, J=8 Hz), 4.10-4.30 (m, 2 H), 3.73 (s, 3 H), 3.72 (s, 3 H), 3.20-3.45 (m, 2 H); 13C NMR (DMSO-d6) δ 169.1, 167.7, 148.5, 148.3, 139.2, 134.5, 131.4, 131.2, 127.9, 126.7, 123.1, 119.5, 111.5, 111.2, 101.9, 55.4, 55.37, 50.6, 41.7, 37.4; Anal. Calcd. for C26H24N2O5. Theoretical: C, 70.26; H, 5.44; N, 6.30. Found: C, 70.12; H, 5.53; N, 6.25.

Sources & evidence

ORD record
ord-705c91f9390d40c5a2f97ab56cd4e90f
Source dataset
uspto-grants-1997_02
Patent number
US05605914

Reaction notes

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