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

HRID 908992Notes

Reaction equation

HRID 908992 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:11])[CH2:5][CH2:4]1.[Cl:30][Si](C)(C)C.CCOCC>CC(CC)=O>[ClH:30].[CH3:29][N:2]([CH3:1])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:11])[CH2:5][CH2:4]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 78%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The less polar diastereoisomer of 2-[4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)-acetamide (64.3 mg, 0.16 mmol) was dissolved in ethyl methyl ketone (10 ml), and chlorotrimethylsilane (0.03 ml, 0.24 mmol) was added. After 2 h ether (10 ml) was added to the reaction mixture and the mixture was stirred at RT for 30 min. The hydrochloride was isolated as a colourless, hygroscopic solid in a yield of 78% (54 mg) (Example 53).

Sources & evidence

ORD record
ord-f0857d72a3eb49658eb75cf8942ad952
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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