Reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[CH:8]1[C:18]2[C:17](=[C:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[CH2:14][S:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:8]1[C:18]2[C:17](=[C:19]3[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6])[CH2:21][CH2:20]3)[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[CH2:14][S:13][C:12]=2[CH:11]=[CH:10][CH:9]=1Participants
5
Procedure
A solution of 10 g of 5-bromo-2-pentanone in 40 cc of chloroform is added dropwise within 10 minutes to a mixture of 14.7 g of 4-(6,11-dihydrodibenzo[b,e]thiepin-11-ylidene)piperidine and 12.7 g of potassium carbonate in 200 cc of chloroform, and the mixture is heated at reflux for 18 hours. After cooling, filtration is effected, the filtrate is washed with water, dried over magnesium sulphate, and the solvent is completely removed by distillation. The oily residue is then chromatographed on 200 g of silica gel with a mixture of chloroform/ethanol 9:1, and the so purified title compound is converted into the hydrogen fumarate form. M.P. 215°-218° from ethanol.
Workup
- temperaturethe mixture is heated
- temperatureat reflux for 18 hours
- temperatureAfter cooling
- filtrationfiltration
- washthe filtrate is washed with water
- dry with materialdried over magnesium sulphate
- customthe solvent is completely removed by distillation
- customThe oily residue is then chromatographed on 200 g of silica gel with a mixture of chloroform/ethanol 9:1
- customthe so purified title compound
Sources & evidence
- ORD record
- ord-49a090cdd1654cd6bdbb4e1731208c2c
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04072756
Linked notes
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