1-tert-Butoxycarbonyl-4-(4-fluorophenylcarbamoyl)-piperazine → N-(4-Fluorophenyl)piperazine-1-carboxamide

HRID 49792Notes

Reaction equation

HRID 49792 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.C(OCC)(=O)C>[F:22][C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:23])=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 98401821-tert-Butoxycarbonyl-4-(4-fluorophenylcarbamoyl)-piperazine

Product 1

HCID 16228149N-(4-Fluorophenyl)piperazine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-tert-Butoxycarbonyl-4-(4-fluorophenylcarbamoyl)-piperazine (0.30 g) was dissolved in a solution of hydrogen chloride in ethyl acetate (4N, 2 ml), and the solution was stirred at ambient temperature for 1 hour. The solvent was removed by evaporation under reduced pressure to give 1-(4-fluorophenylcarbamoyl)piperazine as a white powder, which was taken up into dichloromethane (3 ml), and to the mixture were added in turn pyridine (0.25 ml), 4-trifluoromethoxybenzoyl chloride (0.146 ml), and catalytic amount of N,N-dimethylaminopyridine. After stirring at ambient temperature for 12 hours, the mixture was washed in turn with hydrochloric acid (0.5N), aqueous sodium hydrogen carbonate, and brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was chromatographed on silica gel (50 ml) eluting with 0%-3% methanol in dichloromethane to give 1-(4-fluorophenylcarbamoyl)-4-(4-trifluoromethoxybenzoyl)-piperazine (0.19 g).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-53b38b681f054caaba873f6a82e40bc2
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

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