Dimethylformamide → Ethyl 4-(dibenz[b,e]oxepin-11(6H)-ylidene)-1-piperidinepropionate
Reaction equation
[CH:1]1[C:11]2[C:10](=[C:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:1]1[C:11]2[C:10](=[C:12]3[CH2:17][CH2:16][N:15]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:14][CH2:13]3)[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 3.61 g of 4-(dibenz[b,e]oxepin-11(6H)-ylidene)piperidine, 2.6 g of ethyl 3-bromopropionate, 1.8 g of potassium carbonate and 25 ml of N,N-dimethylformamide was stirred at 80° C. for 2 hrs. After cooling, water was added to the reaction mixture and extracted with ether. The ether layer was washed with water and extracted with hydrochloric acid. The aqueous layer was made alkaline with potassium carbonate and extracted with ether. The ether layer was washed with water, dried and concentrated to give 4.2 g of yellowish brown liquid, which was purified by column chromatography on silica gel (eluent: chloroform) to give 3.9 g of pale yellow liquid.
Workup
- temperatureAfter cooling
- extractionextracted with ether
- washThe ether layer was washed with water
- extractionextracted with hydrochloric acid
- extractionextracted with ether
- washThe ether layer was washed with water
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1ecece786d914257a0bd871fa5431f8c
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05095022
Reaction notes
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