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

HRID 440529Notes

Reaction equation

HRID 440529 reaction equation
[C:1]1([C:11]2([C:14](Cl)=[O:15])[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[CH2:18]([O:25][C:26]1[CH:34]=[CH:33][C:29]([CH2:30][CH2:31][NH2:32])=[CH:28][C:27]=1[O:35][CH3:36])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:18]([O:25][C:26]1[CH:34]=[CH:33][C:29]([CH2:30][CH2:31][NH:32][C:14]([C:11]2([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH2:13][CH2:12]2)=[O:15])=[CH:28][C:27]=1[O:35][CH3:36])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 200381Benzeneethanamine, 3-methoxy-4-(phenylmethoxy)-, hydrochlorideHCID 122764541-(1-Naphthyl)cyclopropanecarbonyl chloride

Product 1

HCID 22406707N-[2-(4-benzyloxy-3-methoxyphenyl)-ethyl]-1-(1-naphthyl)cyclopropane carboxamideYield 101.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1-(1-naphthyl)cyclopropane carbonyl chloride (7.1 g, prepared as described in Example CL32) in ethyl acetate (50 ml) was added to a stirred mixture of 4-benzyloxy-3-methoxyphenethylamine hydrochloride (9.29 g) in ethyl acetate (150 ml). Triethylamine (25 ml) was added and the mixture stirred for a further 64 hours. The organic layer was washed with dilute hydrochloric acid, dried over sodium sulphate and the solvent removed in vacuo to yield N-[2-(4-benzyloxy-3-methoxyphenyl)-ethyl]-1-(1-naphthyl)cyclopropane carboxamide (14.1 g).

Workup

  1. washThe organic layer was washed with dilute hydrochloric acid
  2. dry with materialdried over sodium sulphate
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7514094450c247dfbb39d3c355dee3cc
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

Loading…