[4-Fluoro-3-(trifluoromethyl)phenyl]methanamine → (4-fluoro-3-trifluoromethyl-benzyl)-(1-methyl-1H-benzimidazol-2-yl)-amine

HRID 885448Notes

Reaction equation

Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][C:14]=1[C:21]([F:24])([F:23])[F:22]>CCOC(C)=O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:2]2[N:6]([CH3:7])[C:5]3[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[CH:15][C:14]=1[C:21]([F:22])([F:23])[F:24]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-chloro-1-methyl-1H-benzimidazole (915 mg, 5.5 mmol) and 4-fluoro-3-trifluoromethyl-benzylamine (4.24 g, 22.0 mmol) was stirred at 130° C. overnight. The resulting mixture was diluted with EtOAc, washed with H2O, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by recrystallization from hexane to yield (4-fluoro-3-trifluoromethyl-benzyl)-(1-methyl-1H-benzimidazol-2-yl)-amine MS 324 (M+1)+

Workup

washwashed with H2O
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified by recrystallization from hexane

Sources & evidence

ORD record: ord-81ffa7b9b8b94474bf5adb220217ff77
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242157B2

Reaction notes

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