Reaction #657271

ord-88bdae61eb98419aa9d5aff4c9fe1234

Reaction equation

CC1CCCC(C)N1CC(=O)O.Cl
(2,6-Dimethyl-piperidin-1-yl)-acetic acid hydrochloride
CC1CCCC(C)N1CC(=O)O.Cl
(2,6-Dimethyl-piperidine-1-yl)-acetic acid hydrochloride
O=C1CCC(=O)N1O
N-hydroxysuccinimide
CC1CCCC(C)N1CC(=O)ON1C(=O)CCC1=O
(2,6-Dimethyl-piperidine-1-yl)-acetic acid-(2,5-dioxo-pyrrolidine-1-yl)-ester

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe residue was filtered
  2. 2
    Otherthe filtrate was evaporated in vacuo to dryness
  3. 3
    workup.DISSOLUTIONAfter dissolving the residue in 300 ml CH2Cl2
  4. 4
    Washthe solution was washed with NaHCO3
  5. 5
    Dryingdried over sodium sulphate
  6. 6
    Otherthe solvent was evaporated
  7. 7
    OtherThe compound was then recrystallised from diisopropylether (activated charcoal)

Procedure

12.60 g (60 mMol) (2,6-Dimethyl-piperidin-1-yl)-acetic acid hydrochloride (5), in 100 ml DMF, was added to 7.02 g (60 mMol) N-hydroxysuccinimide and 12.58 g (60 mMol) N,N-dicyclohexylcarbodiimide. The reaction mixture was stirred for 16 h at RT. The residue was filtered and the filtrate was evaporated in vacuo to dryness. After dissolving the residue in 300 ml CH2Cl2, the solution was washed with NaHCO3, dried over sodium sulphate and the solvent was evaporated. The compound was then recrystallised from diisopropylether (activated charcoal).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09023656B2uspto-grants-2015_05