Potassium Carbonate → N-biphenyl-4-yl-3-oxo-3-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-propionamide

HRID 1665608Notes

Reaction equation

Cl.[C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH2:10][C:11](=[O:18])[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]([F:43])([F:42])[F:41]>CN(C=O)C.O>[C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:19])[CH2:10][C:11](=[O:18])[N:12]2[CH2:13][CH2:14][N:15]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:40]([F:41])([F:42])[F:43])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-Biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride (75 mg, 0.2 mmol) and K2CO3 (58 mg, 0.42 mmol) in DMF (2 mL) was stirred for 15 minutes at room temperature, then cooled to 0° C. and 1-bromomethyl-2-trifluoromethyl-benzene (50 mg, 0.21 mmol) was added. The resulting mixture was stirred at room temperature for 6 hours then diluted with water. The resulting precipitate was filtered to afford 85 mg (85%) of N-biphenyl-4-yl-3-oxo-3-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-propionamide. LCMS: 482.2 (M+1)+, 98.8%, 1H NMR: (CDCl3): δ 10.0 (s, 1H), 7.76 (d, 1H), 7.66 (d, 3H), 7.58 (m, 5H), 7.44 (t, 2H), 7.34 (m, 2H), 3.7 (m, 4H), 3.6 (t, 2H), 3.48 (s, 2H).

Workup

filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record: ord-c706af4363314e29ae8507b6b22bdf2f
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039463B2

Reaction notes

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