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

HRID 908923Notes

Reaction equation

HRID 908923 reaction equation
[Cl:1][Si](C)(C)C.[CH3:6][N:7]([CH3:36])[C:8]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:13][CH2:12][C:11](=[CH:14][C:15]([NH:17][CH:18]([CH3:29])[CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:16])[CH2:10][CH2:9]1>CC(CC)=O>[ClH:1].[CH3:36][N:7]([CH3:6])[C:8]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:9][CH2:10][C:11](=[CH:14][C:15]([NH:17][CH:18]([CH3:29])[CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:16])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 115976192-(4-dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide

Product 1

HCID 115976182-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Chlorotrimethylsilane (0.06 ml, 0.48 mmol) was added to a solution of the more polar diastereoisomer of 2-(4-dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)-1-methylethyl]acetamide (133 mg, 0.32 mmol) in ethyl methyl ketone (5 ml) and the mixture was stirred at RT for 1.5 h. The hydrochloride (Example 5) (66 mg, 46%) thereby precipitated out as a colourless solid with an m.p. of 182-186° C.

Workup

  1. customThe hydrochloride (Example 5) (66 mg, 46%) thereby precipitated out as a colourless solid with an m.p. of 182-186° C.

Sources & evidence

ORD record
ord-18d25fbb66394c4db0ed88dff7c4505f
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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