HCID 12595611, compound → 4-(Dimethylamino)-4-phenylcyclohexan-1-one

HRID 2059904Notes

Reaction equation

HRID 2059904 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][CH2:11][C:6]2(OCC[O:7]2)[CH2:5][CH2:4]1>Cl>[CH3:1][N:2]([CH3:19])[C:3]1([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:12][CH2:11][C:6](=[O:7])[CH2:5][CH2:4]1

Participants

3

Reactant 1

HCID 12595611HCID 12595611, compound

Product 1

HCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneYield 67%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

Hydrogen chloride solution (50 ml, 6 mol/l) was added dropwise over 10 min to N,N-dimethyl-8-phenyl-1,4-dioxaspiro[4.5]decan-8-amine (4 g, 14 mmol) at 0° C. The cooling bath was removed and the solution stirred for 16 h at 25° C. Extraction was performed with ethyl acetate (3×50 ml), the aqueous phase was rendered alkaline with sodium hydroxide solution (6 mol/l) (pH=14) and extracted with dichloromethane (4×100 ml). The combined dichloromethane phases were washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated to small volume under vacuum. The crude product was purified by column chromatography (silica gel) with 5% methanol in dichloromethane. Yield: 67%

Workup

  1. customThe cooling bath was removed
  2. extractionExtraction
  3. extractionextracted with dichloromethane (4×100 ml)
  4. washThe combined dichloromethane phases were washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum
  8. customThe crude product was purified by column chromatography (silica gel) with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-ce4fd5a8e2174348ad19e89fcfbb1200
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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