Chlorotrimethylsilane → (4-Dimethylamino-4-phenylcyclohexylidene)acetic acid methyl ester hydrochloride

HRID 908917Notes

Reaction equation

HRID 908917 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]=[C:5]1[CH2:10][CH2:9][C:8]([N:17]([CH3:19])[CH3:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[Cl:21][Si](C)(C)C>CC(CC)=O>[ClH:21].[CH3:1][O:2][C:3](=[O:20])[CH:4]=[C:5]1[CH2:6][CH2:7][C:8]([N:17]([CH3:18])[CH3:19])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 67386136HCID 67386136, compound

Product 1

HCID 67386135(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid methyl ester (2.4 g, 8.7 mmol) was dissolved in ethyl methyl ketone (70 ml), and chlorotrimethylsilane (1.66 ml, 13.17 mmol) was added, while cooling with ice. After a reaction time of 5 h, it was possible to obtain the hydrochloride of the ester as a colourless solid in a yield of 78% (1.95 g) with an m.p. of 204-208° C.

Workup

  1. temperaturewhile cooling with ice
  2. customAfter a reaction time of 5 h, it

Sources & evidence

ORD record
ord-2ce7770afe764fbe8b9e7b255f43bcef
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

Loading…