Diethyl Ether → 2-[4-Dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)-acetamide hydrochloride

HRID 908993Notes

Reaction equation

HRID 908993 reaction equation
[Cl:1][Si](C)(C)C.[CH3:6][N:7]([CH3:34])[C:8]1([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:16])[CH2:10][CH2:9]1.CCOCC>CC(CC)=O>[ClH:1].[CH3:34][N:7]([CH3:6])[C:8]1([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=2)[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:16])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 116334232-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide

Product 1

HCID 116334222-[4-Dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)-acetamide hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Chlorotrimethylsilane (0.132 ml, 1.04 mmol) was added to a solution of the more polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)-acetamide (274 mg, 0.69 mmol) in ethyl methyl ketone (20 ml) and the mixture was stirred at RT for 1 h. Ether (20 ml) was added to the reaction mixture and the mixture was stirred at RT for 1 h. The hydrochloride was obtained as a colourless solid in a yield of 82% (245.5 mg) with an m.p. of 205-207° C. (Example 54).

Workup

  1. stirringthe mixture was stirred at RT for 1 h

Sources & evidence

ORD record
ord-13e2680d34584fd6ae342c304706d661
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

Loading…