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

HRID 430854Notes

Reaction equation

HRID 430854 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:3].Cl.[OH-].[Na+]>O>[CH3:3][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:1]

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)cyclohexanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 g of (+/−)-Tramadol hydrochloride (0.0228 mol) were suspended in 96 ml of water and treated with 32 g of crushed ice. To this suspension was added 26 ml of 36% sodium hydroxide solution. The mixture was then extracted with dichloromethane 140 ml, followed by re-extraction with a further 40 ml of dichloromethane. The organic layers were combined and dried over magnesium sulphate. The solvent was then removed under vacuum to give the (+/−)-Tramadol free base quantitatively as a yellow oil. This was taken up in 48 ml of ethanol and added to a solution of 30 g (L)-(−)-tartaric acid (0.0228 mol) in 224 ml of ethanol. This solution was stirred at 20° C. for two hours, and then allowed to stand for 24 hours at 4° C.

Workup

  1. extractionThe mixture was then extracted with dichloromethane 140 ml
  2. extractionfollowed by re-extraction with a further 40 ml of dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-785bcfeb24b64b9f824eb01c365fcba3
Source dataset
uspto-grants-2001_11
Patent number
US06323368B1

Reaction notes

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