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

HRID 908960Notes

Reaction equation

HRID 908960 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:21])[CH:5]=[C:6]1[CH2:11][CH2:10][C:9]([N:18]([CH3:20])[CH3:19])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1>CO.[Pd]>[ClH:1].[CH3:2][O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:7][CH2:8][C:9]([N:18]([CH3:19])[CH3:20])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 1

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

Product 1

HCID 67386483(4-Dimethylamino-4-phenylcyclohexyl)acetic acid methyl ester hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-charcoal (5%, 90 mg) was added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid methyl ester hydrochloride (1.79 g, 5.77 mmol) in methanol. The reaction mixture was hydrogenated at RT under a pressure of 3 bar for 5 h. The catalyst was separated off over Celite and the filtrate was concentrated. The product was thereby isolated as a colourless, oily compound in a quantitative yield (1.79 g).

Workup

  1. customThe catalyst was separated off over Celite
  2. concentrationthe filtrate was concentrated
  3. customThe product was thereby isolated as a colourless, oily compound in a quantitative yield (1.79 g)

Sources & evidence

ORD record
ord-b4a4860fed49475f8cc780f2edc5de5d
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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