Reaction #476540

ord-9da23056fd224cbeafda48ec16e78cb9

Reaction equation

NCC1(CC(=O)O)CCCCC1
gabapentin
CCCC[N+](CCCC)(CCCC)CCCC.[OH-]
tetrabutylammonium hydroxide
CCCC[N+](CCCC)(CCCC)CCCC.NCC1(CC(=O)[O-])CCCCC1
title compound ( 11 )
CCCC[N+](CCCC)(CCCC)CCCC.NCC1(CC(=O)[O-])CCCCC1
Tetrabutylammonium 1-Aminomethyl-1-Cyclohexane Acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was removed in vacuo
  2. 2
    workup.ADDITIONtoluene (200 mL) was added
  3. 3
    Otherevaporated under reduced pressure two times

Procedure

A solution containing gabapentin (34.4 g, 200 mmol), a 1 M solution of tetrabutylammonium hydroxide in methanol (200 mL, 200 mmol), and additional methanol (200 mL) was stirred at ambient temperature for 14 h. The solvent was removed in vacuo, then toluene (200 mL) was added and evaporated under reduced pressure two times. The title compound (11) was obtained as a thick syrup, and was further dried under high vacuum and used without further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08378137B2uspto-grants-2013_02