Phosphate → 4-Dimethylamino-4-phenylcyclohexanol

HRID 1349388Notes

Reaction equation

HRID 1349388 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.B([O-])=O.[Na+].P([O-])([O-])([O-])=O>C(O)(C)C>[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 145326Sodium metaborateHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-one

Product 1

HCID 111487094-Dimethylamino-4-phenylcyclohexanolYield 81.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.35 g of 4-dimethylamino-4-phenylcyclohexanone were suspended in 25 ml of isopropanol; 620 mg of sodium boranate were added, while cooling with an ice bath, and stirring was carried out overnight at room temperature. 6.5 ml of phosphate buffer (pH 7, Merck-Darmstadt) were added dropwise and the mixture was concentrated. The residue was taken up in 10 ml of water and 20 ml of diethyl ether and rendered alkaline with potassium hydroxide. The phases were separated and extracted three times using 15 ml of diethyl ether each time. The combined organic phases were dried over sodium sulfate, filtered and concentrated. 2.75 g of 4-dimethylamino-4-phenylcyclohexanol were obtained.

Workup

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

Sources & evidence

ORD record
ord-eb43a9c92c3f4ff088654273cf124f81
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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