Homoveratrylamine → N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

HRID 1954046Notes

Reaction equation

HRID 1954046 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][NH2:8].[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].[K+].[Br-]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][NH:8][C:25](=[O:26])[CH2:24][C:18]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:16]([O:15][CH3:14])[CH:17]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 3

HCID 8421HomoveratrylamineHCID 253877Potassium BromideHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 67318N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

Procedure

prepared from 3,4-dimethoxyphenethylamine and 3,4-dimethoxyphenylacetyl chloride; mp 125° C. (lit.17 123-125° C.); IR (KBr) 3327, 3064, 3007, 2916, 2840, 1642, 1608, 1591; 1H NMR δ 2.67 (t, 2H), 3.40-3.47 (m, 4H), 3.83 (s, 6H), 3.86 (s, 3H), 3.88 (s, 3H), 5.30 (brs, 1H), 6.52-6.86 (m, 6H); 13C NMR δ 35.6, 41.2, 43.5, 56.3, 56.4, 70.5, 111.7, 112.2, 115.8, 121.1, 127.5, 127.9, 128.5, 129.1, 131.1, 131.6, 137.3, 148.1, 149.5, 158.5, 171.8.

Workup

  1. custommp 125° C. (lit.17 123-125° C.)

Sources & evidence

ORD record
ord-c4a15354f3014f09ade283ca3d020a7c
Source dataset
uspto-grants-2000_09
Patent number
US06121275

Reaction notes

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