Hydrochloric Acid → (R)-N-(2-(2-(10,11-Dihydro-5H-dibenz[b,f]azepin-5-yl)ethoxy)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][CH2:15][CH2:16][N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:35]CCl>C(O)C.O>[ClH:35].[CH:28]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:17]([CH2:16][CH2:15][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:18]=2[CH:31]=[CH:30][CH:29]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The above ester was dissolved in ethanol (10 ml) and a 12 N sodium hydroxide solution (1.25 ml) was added. The mixture was stirred at room temperature for 4 h. A concentrated hydrochloric acid solution was added until pH 1. Dichloromethane (300 ml) was added followed by water until the solid material was dissolved. The phases were separated and the organic phase was dried over sodium sulphate. The solvent was evaporated in vacuo to give a residue, which was re-evaporated twice with acetone and then recrystallized from a mixture of acetone and ethyl acetate. This afforded 1.4 g (65%) of the title compound.
Workup
- dissolutionwas dissolved
- customThe phases were separated
- dry with materialthe organic phase was dried over sodium sulphate
- customThe solvent was evaporated in vacuo
- customto give a residue, which
- customwas re-evaporated twice with acetone
- customrecrystallized from a mixture of acetone and ethyl acetate
Sources & evidence
- ORD record
- ord-f0b6d701019142bb9872e4796b5b2f81
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05348965
Reaction notes
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