Sodium Carbonate → 4-(ethylenedioxy)-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)carbonyl]piperidine
Reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16](Cl)=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:25]1[CH2:34][O:33][CH:32]2[CH:27]([CH2:28][CH2:29][NH:30][CH2:31]2)[O:26]1>C(OCC)(=O)C>[CH2:25]1[CH2:34][O:33][CH:32]2[CH:27]([CH2:28][CH2:29][N:30]([C:16]([CH:6]3[C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=4[CH2:10][CH2:9][C:8]4[CH:12]=[CH:13][CH:14]=[CH:15][C:7]3=4)=[O:17])[CH2:31]2)[O:26]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 10.9 parts of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carboxylic acid chloride is added 4 parts of anhydrous sodium carbonate and then 6.1 parts of 4-(ethylenedioxy)piperidine. The mixture is stirred overnight and then diluted with ethyl acetate. Sodium carbonate is removed by filtration, the filtrate is washed with 1.2 N hydrochloric acid, 15% aqueous sodium hydroxide, and brine, dried with magnesium sulfate and concentrated to give 4-(ethylenedioxy)-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)carbonyl]piperidine, as a white solid melting at about 148.5°-149.5° C. after recrystallization from cyclohexane. This compound has the following structural formula ##STR23##
Workup
- customSodium carbonate is removed by filtration
- washthe filtrate is washed with 1.2 N hydrochloric acid, 15% aqueous sodium hydroxide, and brine
- dry with materialdried with magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3512e47101444e89ad130298f3cd139a
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04188485
Reaction notes
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