Chlorotrimethylsilane → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide hydrochloride

HRID 908942Notes

Reaction equation

HRID 908942 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][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=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)[CH2:4][CH2:5][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[O:11])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 116914922-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide

Product 1

HCID 116914912-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[5-(1H-indol-3-yl)pentyl]acetamide (81 mg, 0.182 mmol) was dissolved in ethyl methyl ketone (3 ml), and chlorotrimethylsilane (0.035 ml, 0.27 mmol) was added. After 1.5 h the hydrochloride was isolated as a colourless solid with an m.p. of 174-183° C. in a yield of 71% (62 mg).

Sources & evidence

ORD record
ord-af058f1c0bdc476689f5a3c21276ce97
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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