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

HRID 1349390Notes

Reaction equation

HRID 1349390 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 of hydrochloric acid (32 wt. %) were diluted with 120 ml of water; 78.4 g of crude (8-benzyl-1,4-dioxa-spiro[4.5]dec-8-yl)-dimethyl-amine were added to this approximately six molar hydrochloric acid, and stirring was carried out for 24 hours. The reaction mixture was washed three times using 100 ml of diethyl ether each time, rendered alkaline (pH>10) with 100 ml of sodium hydroxide solution (32 wt. %) while cooling with an ice bath, and extracted three times using 100 ml of dichloromethane each time. The extracts were combined, dried over sodium sulfate, filtered and concentrated. 50.4 g of 4-benzyl-4-dimethylamino-cyclohexanone were obtained.

Workup

  1. washThe reaction mixture was washed three times
  2. temperaturewhile cooling with an ice bath
  3. extractionextracted three times
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be48203cd82c4ad39e64a84bbabc99a5
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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