Hydrochloric Acid → Piperidin-4-yl pivalate

HRID 2267705Notes

Reaction equation

HRID 2267705 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>CO.[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15](=[O:20])[C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 668415652,2-Dimethyl-propionic acid 1-benzyl-piperidin-4-yl ester

Product 1

HCID 57464983Piperidin-4-yl pivalate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of piperidine 51 (35.99 g, 130.7 mmol) in methanol is hydrogenated with Pd/C in the presence of one equivalent of HCl (104.5 ml, 130.7 mmol, 1.25M in MeOH). After filtration and evaporation, the crude is taken up in ether and washed with 1N—NaOH and brine. Drying, evaporation and distillation (0.08 mbar, 75-90 C) gave a colourless oil. Yield: 17.98 g (74%).

Workup

  1. filtrationAfter filtration and evaporation
  2. washwashed with 1N—NaOH and brine
  3. customDrying
  4. customevaporation and distillation (0.08 mbar, 75-90 C)
  5. customgave a colourless oil

Sources & evidence

ORD record
ord-6331622090a44f008539bbb5c8ccca71
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

Loading…