Cyclohexanol, 2-((dimethylamino)methyl)-1-(3-methoxyphenyl)-, hydrochloride (1:1) → 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol

HRID 1837182Notes

Reaction equation

HRID 1837182 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>C([O-])([O-])=O.[K+].[K+]>[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

3

Reactant 1

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

Product 1

HCID 55232-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanolYield 86.4%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

Tramadol hydrochloride (145 g) was dissolved in 400 mL of a 10% aqueous K2CO3 solution with magnetic stirring. The clear solution was extracted three times with ethyl acetate, dried with anhydrous Na2SO4 and evaporated to dryness on a rotovap. The oily solid was diluted with toluene and evaporated again to produce a clear oil with some white solid (110 g). The oil was filter through silica (neat) to produce a clear oil (102 g). HPLC Rt=6.794 min.

Workup

  1. extractionThe clear solution was extracted three times with ethyl acetate
  2. dry with materialdried with anhydrous Na2SO4
  3. customevaporated to dryness on a rotovap
  4. additionThe oily solid was diluted with toluene
  5. customevaporated again

Sources & evidence

ORD record
ord-78fd7a14700e4ec8a05597c969ac17a5
Source dataset
uspto-grants-2004_08
Patent number
US06780891B2

Reaction notes

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