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

HRID 1948585Notes

Reaction equation

HRID 1948585 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 mmole) was dissolved in 7.5N hydrochloric acid (36 ml) and stirred for 96 hours at room temperature. After completion of the hydrolysis the reaction mixture was extracted with diethyl ether (2×50 ml). The aqueous phase was made alkaline with 5N sodium hydroxide solution while cooling with ice, extracted with dichloromethane (3×50 ml) and concentrated by evaporation. 4-dimethylamino-4-phenylcyclohexanone (Ket-1) was thus obtained as a yellow solid with a melting point of 1040-108° C. in a yield of 97% (7.4 g).

Workup

  1. customAfter completion of the hydrolysis the reaction mixture
  2. extractionwas extracted with diethyl ether (2×50 ml)
  3. temperaturewhile cooling with ice
  4. extractionextracted with dichloromethane (3×50 ml)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b4844f9567534a859f04c94c75ef27e8
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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