Hydrochloric Acid → Piperidin-4-yl pivalate

HRID 1929005Notes

Reaction equation

HRID 1929005 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-b88f296556d348728c2d5b3d209c50f6
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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