Potassium Carbonate → 4-(4-(4-Chlorophenyl)piperazin-1-yl)butanenitrile
Reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH2:2][CH2:3][CH2:4][C:5]#[N:6])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1Participants
Procedure
To a solution of 4-bromobutanenitrile (1.50 g, 10.17 mmol) in dimethyl formamide (20 ml) were added 1-(4-chlorophenyl)piperazine (2.0 g, 10.17 mmol) and potassium carbonate (2.81 g, 20.34 mmol) at room temperature and the reaction mixture was stirred for 3 h at same temperature. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (50 ml) and the aqueous layer was extracted with ethyl acetate (3×50 ml). The combined organic layer was dried over anhydrous sodium sulphate. The solvent in the organic layer was removed under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 10% ethyl acetate in hexane to yield the title compound (2.32 g, 86% yield).
Workup
- extractionthe aqueous layer was extracted with ethyl acetate (3×50 ml)
- dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
- customThe solvent in the organic layer was removed under reduced pressure
- customto obtain a crude product, which
- customwas purified by column chromatography over silica gel (100-200 mesh)
Sources & evidence
- ORD record
- ord-cbd0d717a5f94c099fbf5a179549cccc
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359367B2
Reaction notes
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