Reaction #554593

ord-54144340562d45cdae022a2331d4e3cd

Reaction equation

COc1cccc(C2(O)CCCCC2CN(C)C)c1.Cl
Tramadol hydrochloride
[Na+].[OH-]
sodium hydroxide
CCOC(C)=O
ethyl acetate
→
COc1cccc(C2(O)CCCCC2CN(C)C)c1
tramadol

Reactants

COc1cccc(C2(O)CCCCC2CN(C)C)c1.Cl
Tramadol hydrochloride
[Na+].[OH-]
sodium hydroxide
CCOC(C)=O
ethyl acetate

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.DISSOLUTIONdissolved
  2. 2
    Otherthe ethyl acetate fraction was collected
  3. 3
    workup.DISTILLATIONFrom this fraction, ethyl acetate was distilled off

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.).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08623387B2uspto-grants-2014_01