Hydrochloric Acid → 4-Benzyl-4-(dimethylamino)cyclohexanone

HRID 1179032Notes

Reaction equation

HRID 1179032 reaction equation
Cl.[CH2:2]([C:9]1([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O>[CH2:2]([C:9]1([N:19]([CH3:20])[CH3:21])[CH2:10][CH2:11][C:12](=[O:13])[CH2:17][CH2:18]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 21093242HCID 21093242, compound

Product 1

HCID 204534784-Benzyl-4-(dimethylamino)cyclohexanoneYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 ml hydrochloric acid (32 wt. %) were diluted with 120 ml water, 78.4 g crude (8-benzyl-1,4-dioxa-spiro[4.5]dec-8-yl)-dimethyl-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 100 ml diethyl ether each time, rendered alkaline (pH>10) with 100 ml sodium hydroxide solution (32 wt. %), while cooling on an ice-bath, 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. 50.4 g 4-benzyl-4-dimethylamino-cyclohexanone were obtained.

Workup

  1. washThe reaction mixture was washed three times with 100 ml diethyl ether each time
  2. temperaturewhile cooling on an ice-bath
  3. extractionextracted three times with 100 ml methylene chloride each time
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dc05edb796b9486bbe1258a1e2bbc839
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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