HCID 12595612, compound → 4-(Dimethylamino)-4-phenylcyclohexan-1-one

HRID 1095484Notes

Reaction equation

HRID 1095484 reaction equation
Cl.[CH3:2][N:3]([CH3:20])[C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH2:6][CH2:5]1>Cl>[CH3:2][N:3]([CH3:20])[C:4]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:13][CH2:12][C:7](=[O:8])[CH2:6][CH2:5]1

Participants

3

Reactant 1

HCID 12595612HCID 12595612, compound

Product 1

HCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Dimethyl-(8-phenyl-1,4-dioxaspiro[4.5]dec-8-yl)amine hydrochloride (10.5 g, 35.2 mmol) was dissolved in 7.5 N hydrochloric acid (36 ml) and the solution was stirred at room temperature for 96 h. When the hydrolysis had ended, the reaction mixture was extracted with diethyl ether (2×50 ml). The aqueous phase was rendered alkaline with 5 N sodium hydroxide solution, while cooling with ice, and extracted with methylene chloride (3×50 ml) and the extract was concentrated. It was possible to isolate 4-dimethylamino-4-phenylcyclohexanone (Ket-10) in this way as a yellow solid with a melting point of 104-108° C. in a yield of 97% (7.4 g).

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether (2×50 ml)
  2. temperaturewhile cooling with ice
  3. extractionextracted with methylene chloride (3×50 ml)
  4. concentrationthe extract was concentrated

Sources & evidence

ORD record
ord-e0dad8ae17ee415cb0d8fe7beef0bbcd
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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