Chlorotrimethylsilane → 2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[3-(1H-indol-3-yl)propyl]-acetamide hydrochloride

HRID 908974Notes

Reaction equation

HRID 908974 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:11])[CH2:5][CH2:4]1.[Cl:32][Si](C)(C)C>CC(CC)=O>[ClH:32].[CH3:31][N:2]([CH3:1])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 115833142-(4-Dimethylamino-4-phenylcyclohexyl)-N-[3-(1H-indol-3-yl)propyl]-acetamide

Product 1

HCID 115833132-(4-Dimethylamino-4-phenylcyclohexyl)-N-[3-(1H-indol-3-yl)propyl]-acetamide hydrochlorideYield 65%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[3-(1H-indol-3-yl)propyl]-acetamide (68 mg, 0.162 mmol) was dissolved in ethyl methyl ketone (5 ml), and chlorotrimethylsilane (0.033 ml, 0.245 mmol) was added. After 3 h it was possible to isolate the product as a colourless solid in a yield of 65% (54 mg) with an m.p. of 162-170° C.

Sources & evidence

ORD record
ord-91db338f34ae4b2397d8599f1d20bd0f
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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