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Triethylamine → Cyclopropane carboxylic acid [3-(5-chloro-2,3-dihydro-benzofuran-4-yl)propyl]-amide

HRID 1602417
Notes
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Reaction equation

HRID 1602417 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH2:9][CH2:8][C:7]=2[C:11]=1[CH2:12][CH2:13][CH2:14][NH2:15].C(N(CC)CC)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>CN(C)C=O.ClCCl>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH2:9][CH2:8][C:7]=2[C:11]=1[CH2:12][CH2:13][CH2:14][NH:15][C:26]([CH:23]1[CH2:25][CH2:24]1)=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 196116663-(5-Chloro-2,3-dihydro-benzofuran-4-yl)propylamine hydrochloride

Product 1

HCID 44214322Cyclopropane carboxylic acid [3-(5-chloro-2,3-dihydro-benzofuran-4-yl)propyl]-amideYield 50%

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(5-chloro-2,3-dihydro-benzofuran-4-yl)-propylamine hydrochloride (142 mg), dimethylformamide (5 drops), triethylamine (0.64 ml) and dichloromethane (5 ml) was stirred in ice for 20 minutes. Cyclopropanecarbonyl chloride (66 mg) was added and stirring continued for 5 hours. The mixture was purified by chromatography on silica eluting with ethyl acetate/hexane (1:1) to give the title compound as a white solid (80 mg).

Workup

  1. stirringstirring
  2. waitcontinued for 5 hours
  3. customThe mixture was purified by chromatography on silica eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-7822fb39f01a40358320921f4a1202ae
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05981572

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes