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

HRID 1602417Notes

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]

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 6228DimethylformamideCatalystHCID 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
Patent number
US05981572

Reaction notes

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