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

HRID 908963Notes

Reaction equation

HRID 908963 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1.[Cl:31][Si](C)(C)C>CC(CC)=O>[ClH:31].[CH3:30][N:2]([CH3:1])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 115394472-(4-Dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)ethyl]acetamide

Product 1

HCID 115394462-(4-Dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)ethyl]acetamide hydrochlorideYield 47%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)ethyl]acetamide (141 mg, 0.35 mmol) was warmed gently in ethyl methyl ketone, and chlorotrimethylsilane (0.066 ml, 0.52 mmol) was added. After 1.5 h it was possible to filter off a beige-coloured, hygroscopic product with suction. The filtrate was reduced to a volume of 5 ml and ether was added. The hydrochloride thereby precipitated out as a colourless solid in a yield of 47% (72 mg). M.p.: 135-140° C.

Workup

  1. filtrationto filter off a beige-coloured, hygroscopic product with suction
  2. additionwas added
  3. customThe hydrochloride thereby precipitated out as a colourless solid in a yield of 47% (72 mg)

Sources & evidence

ORD record
ord-6ee7b0aa40e34e66a59f00f4a1f97d9b
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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