Hydrochloric Acid → 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide hydrochloride
Reaction equation
[CH3:1][N:2]([CH3:32])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH:13]([CH3:24])[CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1.[ClH:33]>C(O)C>[ClH:33].[CH3:32][N:2]([CH3:1])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH:13]([CH3:24])[CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide (139 mg, 0.32 mmol) was dissolved in ethanol (10 ml) with gentle heating, 5 M isopropanolic hydrochloric acid (0.096 ml, 0.48 mmol) was added and the mixture was stirred at RT for 2 h. The clear solution was concentrated to approx. 1 ml and the residue was stirred with ether (10 ml) for 20 h. The solid thereby formed was filtered off with suction. The more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide hydrochloride was obtained in this way as a pink-coloured solid in a yield of 93.5 mg (62%).
Workup
- additionwas added
- concentrationThe clear solution was concentrated to approx. 1 ml
- stirringthe residue was stirred with ether (10 ml) for 20 h
- customThe solid thereby formed
- filtrationwas filtered off with suction
Sources & evidence
- ORD record
- ord-648c11f9ad8d4badb55c6ceebf44175b
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017630B2
Reaction notes
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