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

HRID 1643955Notes

Reaction equation

HRID 1643955 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-a791f2b56147422d82e3d7186c20714d
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

Loading…