Chlorotrimethylsilane → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(3-phenyl-propyl)acetamide hydrochloride

HRID 908925Notes

Reaction equation

HRID 908925 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:11])[CH2:5][CH2:4]1.[Cl:29][Si](C)(C)C>CC(CC)=O>[ClH:29].[CH3:28][N:2]([CH3:1])[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:8][CH2:7][C:6](=[CH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:11])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 115171962-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(3-phenyl-propyl)acetamide

Product 1

HCID 115171952-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(3-phenyl-propyl)acetamide hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(3-phenyl-propyl)acetamide (203 mg, 0.536 mmol) was dissolved in ethyl methyl ketone (12 ml) with gentle heating and chlorotrimethylsilane (0.101 ml, 0.8 mmol) was added. After 2 h it was possible to isolate the product as a colourless solid in a yield of 95% (211 mg) with an m.p. of 225-230° C.

Workup

  1. temperaturewith gentle heating

Sources & evidence

ORD record
ord-0fdbcdd6d33d4984b565f68150610fc6
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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