Methyl iodide → (4-Methyl-3-phenyl-piperazin-1-yl)-(2'-trifluoromethyl-biphenyl-4-yl)-methanone

HRID 737127Notes

Reaction equation

[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:30])([F:29])[F:28])=[CH:17][CH:16]=3)=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:31](N(CC)C(C)C)(C)C.IC>C(#N)C.ClCCl>[CH3:31][N:12]1[CH2:11][CH2:10][N:9]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:29])([F:30])[F:28])=[CH:17][CH:16]=2)=[O:14])[CH2:8][CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

This compound could be made in the following manner: 100 mg of (3-phenyl-piperazin-1-yl)-(2′-trifluoromethyl-biphenyl-4-yl)-methanone would be dissolved in 3 mL of acetonitrile, 2 equiv. of N,N-diisopropylethylamine would be added followed by 1.1 equiv. of iodomethane. The reaction would be heated to 80° C. overnight. After cooling to room temperature, the reaction would be diluted with dichloromethane and washed with 1M aqueous sodium hydroxide solution, dried over sodium sulfate and concentrated in vacuo. The crude residue would be purified by column chromatography to afford the title compound.

Workup

customThe reaction
temperatureAfter cooling to room temperature
customthe reaction
washwashed with 1M aqueous sodium hydroxide solution
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude residue would be purified by column chromatography

Sources & evidence

ORD record: ord-2e91792237974161a3b22a1bb6a892a9
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595397B2

Reaction notes

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