Reaction #1393

Reaction equation

(1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol L-(+)-tartrate

caustic soda

→

(1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol

Yield 99.0%

Solvents

water

Conditions

Workup

1. 1
   workup.ADDITIONtreated with 900 g
2. 2
   Othercrushed ice
3. 3
   ExtractionThe mixture was subsequently extracted with 2500 ml dichloromethane
4. 4
   Extractionwas extracted with a further 500 ml dichloromethane
5. 5
   Otherafter phase separation
6. 6
   DryingThe combined organic phases were dried over sodium sulphate
7. 7
   OtherAfter removing the solvent
8. 8
   workup.DISTILLATIONby distillation

Procedure

2050 g (4.95 mole) (1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol L-(+)-tartrate from step 2 were dissolved in 4000 ml water and treated with 900 g crushed ice. 1000 ml of 36-38% (technical) caustic soda solution were added drop-wise with stirring. The mixture was subsequently extracted with 2500 ml dichloromethane, and was extracted with a further 500 ml dichloromethane after phase separation. The combined organic phases were dried over sodium sulphate. After removing the solvent by distillation, 1280 g (99% theoretical) of (1S,2S)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol were obtained as a syrup.

Source