4-Fluoro-2-(trifluoromethyl)benzonitrile → (2S,5R)-4-(4-Benzyl-2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile

HRID 1838240Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][C@H:12]([CH3:14])[NH:11][CH2:10][C@H:9]1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=1>N1C=CC=CC=1>[CH2:1]([N:8]1[C@H:9]([CH3:15])[CH2:10][N:11]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:26])([F:28])[F:27])[CH:18]=2)[C@@H:12]([CH3:14])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A 15 ml portion of pyridine solution containing 0.63 g of (2R,5S)-1-benzyl-2,5-dimethylpiperazine was mixed with 0.7 g of 4-fluoro-2-trifluoromethylbenzonitrile and stirred at 90° C. for 2 days. The reaction mixture was concentrated and the residue was purified by a silica gel column chromatography to obtain the title compound from n-hexane-ethyl acetate (9:2, v/v) as a white solid.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record: ord-7db6d398660b42efacee3b3caa0e42ed
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673799B1

Reaction notes

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