Hydrochloric Acid → 4-(Dimethylamino)-4-phenylcyclohexan-1-one

HRID 1179029Notes

Reaction equation

HRID 1179029 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>O>[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

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 12595611HCID 12595611, compound

Product 1

HCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

165 ml hydrochloric acid (32 wt. %) were diluted with 100 ml water, 60.0 g dimethyl-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)-amine were added to this approx. six molar hydrochloric acid and the mixture was stirred for 24 hours. The reaction mixture was washed three times with 50 ml diethyl ether each time, rendered alkaline (pH>10) with 100 ml sodium hydroxide solution (32 wt. %) and extracted three times with 100 ml methylene chloride each time. The extracts were combined, dried over sodium sulfate and filtered and the filtrate was concentrated. 36.1 g 4-dimethylamino-4-phenyl-cyclohexanone were obtained.

Workup

  1. washThe reaction mixture was washed three times with 50 ml diethyl ether each time
  2. extractionextracted three times with 100 ml methylene chloride each time
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-932c4844b78d4dd889f87e6526bcdc80
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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