4-Fluorobenzoyl chloride → Phenylmethyl 4-[(4-fluorobenzoyl)amino]-1-piperazinecarboxylate

HRID 726173Notes

Reaction equation

HRID 726173 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>C(N(CC)CC)C>[CH2:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][N:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=2)[CH2:7][CH2:6]1)=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 19710621HCID 19710621, compound

Product 1

HCID 9928674Phenylmethyl 4-[(4-fluorobenzoyl)amino]-1-piperazinecarboxylateYield 64.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Crude 1-amino-4-benzyloxycarbonylpiperazine (433 g) and triethylamine (254 ml) were dissolved in dry methylene chloride(1.81) and to this solution was added dropwise p-fluorobenzoyl chloride (225 g) under cooling in an ice-bath at 8~25° C. for a period of 20 minutes. The reaction mixture was stirred for 1 hour at ambient temperature and then the resultant crystal was collected by filtration and washed with methylene chloride (300 ml), diisopropyl ether (500 ml) and water (1.51) successively to give N-(4-benzyloxycarbonyl-1-piperazinyl)-4-fluorobenzamide (327 g) as a white powder.

Workup

  1. temperatureunder cooling in an ice-bath at 8~25° C. for a period of 20 minutes
  2. filtrationthe resultant crystal was collected by filtration
  3. washwashed with methylene chloride (300 ml), diisopropyl ether (500 ml) and water (1.51) successively

Sources & evidence

ORD record
ord-9764b7912e5c4658bb2e33b75084bc59
Source dataset
uspto-grants-1998_01
Patent number
US05708172

Reaction notes

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