2-(4-Fluorophenyl)acetic acid → N-Cyclopropyl-2-(4-fluorophenyl)acetamide

HRID 1351258Notes

Reaction equation

HRID 1351258 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C)C=O.O>[CH:12]1([NH:15][C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 98372-(4-Fluorophenyl)acetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 21098726N-Cyclopropyl-2-(4-fluorophenyl)acetamideYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluorophenylacetic acid (4.5 g) and cyclopropylamine (1.7 g) in N,N-dimethylformamide (60 mL) was added 1-Hydroxybenzotriazole (4.4 g), followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (WSC) hydrochloride (6.2 g) on an ice bath. This solution was stirred for 4.5 hours while gradually warming to room temperature. The reaction solution was poured into water (120 mL) on an ice bath, and the resulting solid was collected by filtration, washed with water, then dried, and the title compound (4.19 g) was obtained as a colorless solid.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-a463893a2c434d32b3da73166255e073
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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