Sodium Hydroxide → 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol

HRID 1296Notes

Reaction equation

HRID 1296 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[OH:12])[CH3:4].[OH-].[Na+]>O>[CH3:4][N:3]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[OH:12])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9971980Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, hydrochloride (1:1)

Product 1

HCID 55232-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 kg (10 mole) (1RS,2RS)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol hydrochloride (1) were suspended in 4800 ml water and treated with 1.6 kg crushed ice. 1300 ml of 36-38% (technical) caustic soda solution were added drop-wise with stirring. The mixture was subsequently extracted with 7000 ml dichloromethane, and was extracted with a further 2000 ml dichloromethane after phase separation. The combined organic phases were dried over sodium sulphate. After removing the solvent by distillation, 2630 g (99% theoretical) of (1RS,2RS)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol were obtained as a syrup.

Workup

  1. additiontreated with 1.6 kg
  2. customcrushed ice
  3. extractionThe mixture was subsequently extracted with 7000 ml dichloromethane
  4. extractionwas extracted with a further 2000 ml dichloromethane
  5. customafter phase separation
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. customAfter removing the solvent
  8. distillationby distillation

Sources & evidence

ORD record
ord-822a168440d44234b23b8b29fa23f00d
Source dataset
uspto-grants-1998_03
Patent number
US05723668

Reaction notes

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