Potassium Carbonate → Biphenyl-4-carboxylicacid {2-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-2-oxo-ethyl}-amide

HRID 1178016Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].OC(C(F)(F)F)=O.[O:14]=[C:15]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)[CH2:16][NH:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=[O:19].[F:38][C:39]([F:49])([F:48])[C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=1[CH2:42]Br>CN(C=O)C>[F:38][C:39]([F:48])([F:49])[C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=1[CH2:42][N:35]1[CH2:36][CH2:37][N:32]([C:15](=[O:14])[CH2:16][NH:17][C:18]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)=[O:19])[CH2:33][CH2:34]1

Participants

Conditions

Temperature: 90 °C

Procedure

K2CO3 (50.5 mg, 0.37 mmol) was added to a stirred solution of biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA salt (80 mg, 0.18 mmol) in DMF (3 mL). 2-Trifluoromethyl benzyl bromide (52.2 mg, 0.22 mmol) was then added, and the resulting mixture was heated to 90° C. overnight. The product was extracted with ethyl acetate and the ethyl acetate layer was washed with saturated brine solution, dried over sodium sulphate and concentrated to afford 48 mg (45.7% yield) of biphenyl-4-carboxylicacid {2-[4-(2-trifluoromethyl-benzyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LC-MS purity: 94.3%, 1H NMR: (CDCl3) δ 7.9 (d, 2H), 7.8-7.7 (d, 1H), 7.7-7.6 (m, 5H), 7.55 (m, 1H), 7.5 (m, 2H), 7.4 (m, 3H), 4.3 (d, 2H), 3.7 (s, 4H), 3.5 (t, 2H), 2.5 (q, 4H).

Workup

extractionThe product was extracted with ethyl acetate
washthe ethyl acetate layer was washed with saturated brine solution
dry with materialdried over sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-1972d0816bf5459c9e85a9aff299c404
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842696B2

Reaction notes

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