Chlorotrimethylsilane → 2-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone hydrochloride

HRID 2357490Notes

Reaction equation

HRID 2357490 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1.[Cl:34][Si](C)(C)C>CC(CC)=O>[ClH:34].[CH3:33][N:2]([CH3:1])[C:3]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[CH2:13]2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 99825912-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone

Product 1

HCID 99825902-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone hydrochlorideYield 65%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-dimethylamino-4-phenylcyclohexyl)-1-[3-(1H-indol-3-yl)piperidine-1-yl]-ethanone (66 mg, 0.148 mmole) was dissolved in ethyl methyl ketone (4 ml) and chlorotrimethylsilane (0.03 ml, 0.23 mmole) was added. After 1 hour the hydrochloride was isolated as a colourless solid in a yield of 65% (46 mg) (Example 53). A melting point could not be determined. The hydrochloride was obtained as a diastereoisomer mixture.

Sources & evidence

ORD record
ord-a67bb9b81fed40a6a581fee77f122379
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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