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

HRID 908920Notes

Reaction equation

HRID 908920 reaction equation
[Cl:1][Si](C)(C)C.[CH3:6][N:7]([CH:9]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:11][C:10]1=[CH:21][C:22]([NH:24][CH2:25][CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)=[O:23])[CH3:8]>CC(CC)=O>[ClH:1].[CH3:6][N:7]([CH:9]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:11][C:10]1=[CH:21][C:22]([NH:24][CH2:25][CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)=[O:23])[CH3:8]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 673864932-(Dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)ethyl]acetamide

Product 1

HCID 673865972-(Dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)ethyl]acetamide hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Chlorotrimethylsilane (0.034 ml, 0.26 mmol) was added to the solution of 2-(dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)ethyl]acetamide (75 mg, 0.178 mmol) in ethyl methyl ketone (15 ml). After 2 h it was possible to isolate the hydrochloride as a beige-coloured solid in a yield of 75% (61 mg) with an m.p. of 203-207° C.

Sources & evidence

ORD record
ord-11949c46d241454d9c9dcf307a1fef19
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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