2,3-Dimethoxyphenethylamine → N-(2, 3-dimethoxyphenylethyl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 1954047Notes

Reaction equation

HRID 1954047 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][NH2:7].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:24][C:25](Cl)=[O:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[CH2:5][CH2:6][NH:7][C:25](=[O:26])[CH2:24][C:18]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:16]([O:15][CH3:14])[CH:17]=1

Participants

3

Reactant 2

HCID 1378582,3-DimethoxyphenethylamineHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 22742672N-(2, 3-dimethoxyphenylethyl)-2-(3,4-dimethoxyphenyl)acetamide

Procedure

prepared from 2,3-dimethoxyphenethylamine (Lindemann, Helv. Chim. Acta. 1949, 32, 69-75) and 3,4-dimethoxyphenylacetyl chloride; mp 80° C. (lit.29 79-80° C.); IR 3315, 2962, 2838, 1636, 1593, 1548; 1H NMR δ 2.61 (t, 2H), 3.22-3.30 (m, 4H), 3.58 (s, 3H), 3.64 (s, 6H), 3.67 (s, 3H), 6.22 (brs, 1H), 6.44-6.79 (m, 6H); 13C NMR δ 30.0, 41.0, 43.7, 55.9, 56.2, 56.3, 60.9, 111.2, 111.9, 112.9, 122.0, 122.6, 124.4, 127.9, 133.1, 147.5, 148.5, 149.5, 153.1, 171.9.

Workup

  1. custommp 80° C. (lit.29 79-80° C.)

Sources & evidence

ORD record
ord-55296d6af4d14de4a1e74d49635d8ace
Source dataset
uspto-grants-2000_09
Patent number
US06121275

Reaction notes

Loading…