1-(3-Chlorophenyl)piperazine → 4-(3-Chlorophenyl)-1-(2,3-epoxypropyl)piperazine
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:16][CH:18]3[O:20][CH2:19]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
To a mixture of 1.50 g of 4-(3-chlorophenyl)piperazine and 0.31 g of sodium hydride was added 2.4 ml of epichlorohydrin and the reaction mixture was stirred at room temperature for 30 minutes. After the reaction was completed, the reaction mixture was extracted with 100 ml of ethyl acetate, and the extract was washed 5 times with 100 ml of water, then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain the residue which was purified by means of a silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:1) to obtain 1.66 g of 4-(3-chlorophenyl) -1-(2,3-epoxypropyl)piperazine as in the form of an oily substance.
Workup
- extractionthe reaction mixture was extracted with 100 ml of ethyl acetate
- washthe extract was washed 5 times with 100 ml of water
- dry with materialdried with anhydrous magnesium sulfate
- customThe solvent was removed by evaporation
- customto obtain the residue which
- customwas purified by means of a silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:1)
Sources & evidence
- ORD record
- ord-5ce8719f490b42938129e2c21a99a0d9
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05055474
Reaction notes
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