Hydrochloric Acid → (R)-1-(3-(9H-Tribenz[b,d,f]azepine-9-yl)propyl)-3-piperidinecarboxylic acid, hydrochloride
Reaction equation
[ClH:1].C([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][CH2:14][CH2:15][N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20]3[CH:27]=[CH:28][CH:29]=[CH:30][C:19]=3[C:18]3[CH:31]=[CH:32][CH:33]=[CH:34][C:17]2=3)[CH2:8]1)=[O:6])C.Cl>C(O)C.[OH-].[Na+]>[ClH:1].[CH:30]1[C:19]2[C:18]3[CH:31]=[CH:32][CH:33]=[CH:34][C:17]=3[N:16]([CH2:15][CH2:14][CH2:13][N:9]3[CH2:10][CH2:11][CH2:12][C@@H:7]([C:5]([OH:6])=[O:4])[CH2:8]3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[C:20]=2[CH:27]=[CH:28][CH:29]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
The above ester (0.13 g, 0.27 mmol) was dissolved in ethanol (3 ml) and 2N sodium hydroxide (0.6 ml). The mixture was stirred at room temperature for 1.5 hour, acidified by addition of 1N hydrochloric acid (pH 1) and ethanol was removed in vacuo. The aqueous solution was diluted with water (10 ml), washed with diethyl ether (20 ml) and extracted with dichloromethane (30 ml). The organic extract was dried (MgSO4) and concentrated in vacuo to afford 90 mg (74%) of the title compound as a solid.
Workup
- customwas removed in vacuo
- additionThe aqueous solution was diluted with water (10 ml)
- washwashed with diethyl ether (20 ml)
- extractionextracted with dichloromethane (30 ml)
- extractionThe organic extract
- dry with materialwas dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-77571e7262b9455bb2c38e4b470233f3
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05716949
Reaction notes
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