Hydrochloric Acid → (R)-N-(2-((10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)methoxy)ethyl)-3-piperidinecarboxylic acid hydrochloride
Reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH:15]=[C:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].O.[ClH:34]>C(O)C.ClCCl>[ClH:34].[CH:27]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:16](=[CH:15][O:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:17]=2[CH:30]=[CH:29][CH:28]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
The above ester (2.0 g, 4.9 mmol) was dissolved in ethanol (20 ml) and a 4 N sodium hydroxide solution (4.9 ml) was added. The mixture was stirred at 50° C. for 2 h. Water (10 ml) was added and ethanol was evaporated in vacuo to give an aqueous residue. A 4 M aqueous hydrochloric acid solution (6.2 ml) was added followed by dichloromethane (50 ml). The phases were separated and the aqueous phase was extracted with dichloromethane (50 ml). The combined organic phases were washed with water (10 ml) and then dried over magnesium sulphate. The solvent was evaporated in vacuo and the residue dried in vacuo to give 1.71 g of the title compound as a solid.
Workup
- customethanol was evaporated in vacuo
- customto give an aqueous residue
- customThe phases were separated
- extractionthe aqueous phase was extracted with dichloromethane (50 ml)
- washThe combined organic phases were washed with water (10 ml)
- dry with materialdried over magnesium sulphate
- customThe solvent was evaporated in vacuo
- customthe residue dried in vacuo
Sources & evidence
- ORD record
- ord-e012b1090b164fa18eb7f4f26ba53a68
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05348965
Reaction notes
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