Water → N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide

HRID 440501Notes

Reaction equation

HRID 440501 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:12](Cl)=[O:13])[CH2:11][CH2:10]1.Cl.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][C:25]=1[O:33][CH3:34])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C(OCC)(=O)C.C(N(CC)CC)C>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][C:12]([C:9]2([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:11][CH2:10]2)=[O:13])=[CH:26][C:25]=1[O:33][CH3:34])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 200381Benzeneethanamine, 3-methoxy-4-(phenylmethoxy)-, hydrochlorideHCID 242737911-(2-Methoxyphenyl)cyclopropane-1-carbonyl chloride

Product 1

HCID 22406839N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1-(2-methoxyphenyl)cyclopropane carbonyl chloride (16 g) in ethyl acetate (50 ml) was added to a stirred solution of 4-benzyloxy-3-methoxyphenylethylamine hydrochloride (22.3 g) in ethyl acetate (250 ml) and triethylamine (30 ml). The mixture was stirred for 3 days then water was added. The organic layer was washed with 5M-HCl, then water, then 2M aqueous sodium hydroxide solution, and dried over sodium sulphate. Evaporation yielded N-[2-(4-benzyloxy-3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)cyclopropane carboxamide.

Workup

  1. washThe organic layer was washed with 5M-HCl
  2. dry with materialwater, then 2M aqueous sodium hydroxide solution, and dried over sodium sulphate
  3. customEvaporation

Sources & evidence

ORD record
ord-04d524925911480f91e1b27085158959
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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