Phosphate → HCID 21093239, compound

HRID 1349391Notes

Reaction equation

HRID 1349391 reaction equation
[CH2:1]([C:8]1([N:15]([CH3:17])[CH3:16])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B([O-])=O.[Na+].P([O-])([O-])([O-])=O>C(O)(C)C>[CH2:1]([C:8]1([N:15]([CH3:16])[CH3:17])[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 145326Sodium metaborateHCID 204534784-Benzyl-4-(dimethylamino)cyclohexanone

Product 1

HCID 21093239HCID 21093239, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

40.0 g of 4-benzyl-4-dimethylamino-cyclohexanone were suspended in 250 ml of isopropanol; 19.9 g of sodium boranate were added, while cooling with an ice bath, and stirring was carried out overnight at room temperature. 65 ml of phosphate buffer (pH 7, Merck-Darmstadt) were added dropwise and the mixture was concentrated. The residue was taken up in water and dichloromethane and rendered alkaline with potassium hydroxide. The phases were separated and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 37.7 g of 4-benzyl-4-dimethylaminocyclohexanol were obtained.

Workup

  1. temperaturewhile cooling with an ice bath
  2. concentrationthe mixture was concentrated
  3. customThe phases were separated
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae328603d26f420cb7dcde898ae5675e
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

Loading…