Triethylamine → Cyclopropanecarboxylic acid [3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)propyl]amide

HRID 1602419Notes

Reaction equation

HRID 1602419 reaction equation
[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>ClCCl>[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[C:5]([CH2:11][CH2:12][CH2:13][NH:14][C:25]([CH:22]2[CH2:24][CH2:23]2)=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 196116493-(7-Fluoro-2,3-dihydro-benzofuran-4-yl)-propylamine

Product 1

HCID 54235850Cyclopropanecarboxylic acid [3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)propyl]amideYield 10.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(7-fluoro-2,3-dihydro-benzofuran-4-yl)-propylamine (114 mg), triethylamine (0.089 ml), dichloromethane (5 ml) and cyclopropanecarbonyl chloride (67 mg) was stirred in ice for 20 minutes and stirring continued at room temperature overnight. The mixture was partitioned between 2N hydrochloric acid and dichloromethane and the organic phase washed with 8% sodium bicarbonate and evaporated. Purification of the residue by preparative hplc gave the title compound as a white solid (16 mg).

Workup

  1. stirringstirring
  2. waitcontinued at room temperature overnight
  3. customThe mixture was partitioned between 2N hydrochloric acid and dichloromethane
  4. washthe organic phase washed with 8% sodium bicarbonate
  5. customevaporated
  6. customPurification of the residue by preparative hplc

Sources & evidence

ORD record
ord-cf80e80104c3420bb674f3d80f12c322
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

Loading…