Potassium Carbonate → HCID 15143635, compound

HRID 1086240Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:22]1([NH:32][C:33](=[O:36])[CH2:34]Cl)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:34][C:33](=[O:36])[NH:32][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[CH2:13][CH2:14]2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 290 mg of 1-[bis(4-fluorophenyl)methyl]piperazine and 400 mg of N-(1-naphthyl)chloroacetamide was dissolved in 10 ml of a 1:1 by volume mixture of tetrahydrofuran and N,N-dimethylformamide. 1.2 g of anhydrous potassium carbonate were then added to the solution, after which the reaction mixture was stirred for 15 hours at 25° C. and then diluted with ethyl acetate. The organic layer was washed three times with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure. The residue was subjected to silica gel thin layer chromatography using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the developing solvent, to afford 430 mg of 1-[bis(4-fluorophenyl)methyl]4-(1-naphthylcarbamoylmethyl)piperazine, melting at 173° C.

Workup

washThe organic layer was washed three times with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated off under reduced pressure
additionby volume mixture of cyclohexane and ethyl acetate as the developing solvent

Sources & evidence

ORD record: ord-40204e0d99974416b15654bb7da4a9e8
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05028610

Reaction notes

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