Chlorotrimethylsilane → 2-(4-Dimethylamino-4-phenylcyclohexyl)-N-(1H-indol-3-ylmethyl)acetamide hydrochloride

HRID 908971Notes

Reaction equation

HRID 908971 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:11])[CH2:5][CH2:4]1.[Cl:30][Si](C)(C)C>CC(CC)=O>[ClH:30].[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 115970632-(4-Dimethylamino-4-phenylcyclohexyl)-N-(1H-indol-3-ylmethyl)acetamide

Product 1

HCID 115970622-(4-Dimethylamino-4-phenylcyclohexyl)-N-(1H-indol-3-ylmethyl)acetamide hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Dimethylamino-4-phenylcyclohexyl)-N-(1H-indol-3-ylmethyl)acetamide (213 mg, 0.54 mmol) was dissolved in ethyl methyl ketone with gentle heating and chlorotrimethylsilane (0.103 ml, 0.82 mmol) was added. After 1.5 h it was possible to obtain the hydrochloride as a colourless solid in a yield of 93% (214 mg) with an m.p. of 233-235° C.

Workup

  1. temperaturewith gentle heating

Sources & evidence

ORD record
ord-1c5019a7f4b0498f97f067b41434aae7
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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