1-Benzyl-4-(N-Boc-amino)piperidine → 4-(N-Boc-amino)piperidine

HRID 19463Notes

Reaction equation

HRID 19463 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:18]([O:17][C:15]([NH:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 44386181-Benzyl-4-(N-Boc-amino)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 7238334-(N-Boc-amino)piperidineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyl-4-tertbutyloxycarbonylaminopiperidine 5 (7.95 g; 27.4 mmol) in 120 ml of MeOH is poured into a hydrogenation reactor. 10% Pd/c-based catalyst is added (1.46 g; 1.38 mmol) and the mixture is subjected to a hydrogen pressure of 3.5 bars (50 psi) for 24 hours in a Parr type shaker. After filtration on celite and washing with methanol, the medium is concentrated in order to produce 4.98 g (Yield=91%) of product in the form of white crystals.

Workup

  1. filtrationAfter filtration on celite
  2. washwashing with methanol
  3. concentrationthe medium is concentrated in order

Sources & evidence

ORD record
ord-7fbbc4b12374417a9e72e3284df826eb
Source dataset
uspto-grants-2010_06
Patent number
US07745413B2

Reaction notes

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