(4-Benzylpiperazin-1-yl)-(4-trifluoromethylphenyl)amine → Piperazin-1-yl-(4-trifluoromethylphenyl)amine

HRID 856060Notes

Reaction equation

C([N:8]1[CH2:13][CH2:12][N:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[N:11]1([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (4-benzylpiperazin-1-yl)-(4-trifluoromethylphenyl)amine prepared in Reference Example 108 and 10% palladium/carbon (0.53 g) in ethanol (50 ml) was stirred at room temperature under an atmospheric pressure of hydrogen for 6 hours, and then at 60° C. for 10 hours. After the catalyst was removed by filtration through Celite, 10% palladium/carbon (0.53 g) was added to the filtrate, and the mixture was stirred at 60° C. under an atmospheric pressure of hydrogen for 8 hours. After the catalyst was removed by filtration through Celite, the filtrate was concentrated under reduced pressure. The resulting solid was dried in vacuo to afford piperazin-1-yl-(4-trifluoromethylphenyl)amine (1.76 g, yield 90%) as a colorless crystalline powder.

Workup

customAfter the catalyst was removed by filtration through Celite, 10% palladium/carbon (0.53 g)
additionwas added to the filtrate
customAfter the catalyst was removed by filtration through Celite
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting solid was dried in vacuo

Sources & evidence

ORD record: ord-7078ba9038ca44ab904a8d1407c24d0d
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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