Water → Methyl 4-(4-benzyl-1-piperazinyl)-3-trifluoromethyl-benzoate

HRID 430487Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

7 g (31.5 mmol) of methyl 4-fluoro-3-trifluoromethyl-benzoate are dissolved in 60 ml of dry dimethylsulphoxide (DMSO) and combined with 5.55 g (31.5 mmol) of N-benzylpiperazine and 4.35 g (31.5 mmol) of potassium carbonate. The mixture is stirred for 12 hours at 90° C. After cooling, the reaction mixture is poured into 200 ml of water and extracted three times with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution, dried over magnesium sulphate and distilled off in vacuo. The residue is chromatographed on silica gel with a mixture of ethyl acetate and n-heptane.

Workup

temperatureAfter cooling
extractionextracted three times with ethyl acetate
washThe combined organic phases are washed with water and saturated sodium chloride solution
dry with materialdried over magnesium sulphate
distillationdistilled off in vacuo
customThe residue is chromatographed on silica gel with a mixture of ethyl acetate and n-heptane

Sources & evidence

ORD record: ord-b2c1e2f2a8804ffb91297a8ddf863699
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323207B1

Reaction notes

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