Formic Acid → tert-Butyl 4-(piperazin-1-yl)piperidine-1-carboxylate

HRID 1631972Notes

Reaction equation

HRID 1631972 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)=O>CO.[Pd]>[N:14]1([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 18971584Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 17750358tert-Butyl 4-(piperazin-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3.01 g (7.46 mmol) of benzyl 4-(1-tert-butoxycarbonylpiperidin-4-yl)piperazine-1-carboxylate and 300 mg of Pd—C (5%) in 100 ml of methanol was mixed with 4 ml of formic acid and stirred under a hydrogen atmosphere (1 bar) at room temperature overnight. The reaction mixture was filtered through Celite, the residue on the filter was washed with methanol, and the solvent was then removed in vacuo. The residue was used without further purification in the next reaction step.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe residue on the filter was washed with methanol
  3. customthe solvent was then removed in vacuo
  4. customThe residue was used without further purification in the next reaction step

Sources & evidence

ORD record
ord-8ba3f999a16d423eaadad235ef330b09
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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