Ethyl Acetate → 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol

HRID 467411Notes

Reaction equation

HRID 467411 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+].C(OCC)(=O)C>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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 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

Tramadol hydrochloride was dissolved in purified water. To this solution, approximately 1.5-fold molar amount of sodium hydroxide was added and dissolved therein. Then, approximately 2-fold volume of ethyl acetate was further added thereto, and the ethyl acetate fraction was collected using a separatory funnel. From this fraction, ethyl acetate was distilled off to obtain tramadol (pKa 9.41) as oil. This tramadol and an equimolar amount of 2-ethylhexanoic acid were added to methanol and uniformly mixed. Then, methanol was distilled off to synthesize 2-ethylhexanoate of tramadol as viscous oil. The obtained viscous oil was directly applied to rock salt plates and measured for its infrared absorption spectrum (FTIR8400S manufactured by Shimadzu Corp.).

Workup

  1. dissolutiondissolved
  2. customthe ethyl acetate fraction was collected
  3. distillationFrom this fraction, ethyl acetate was distilled off

Sources & evidence

ORD record
ord-54144340562d45cdae022a2331d4e3cd
Source dataset
uspto-grants-2014_01
Patent number
US08623387B2

Reaction notes

Loading…