Hydrochloric Acid → 1-[4-Hydroxy-1-(4-pyridyl)piperidin-4-ylmethy]-2-piperazinone Hydrochloride

HRID 1840547Notes

Reaction equation

HRID 1840547 reaction equation
C(OC([N:11]1[CH:16]=[CH:15][N:14]([CH2:17][C:18]2([OH:30])[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[C:13](=[O:31])[CH2:12]1)=O)C1C=CC=CC=1.[ClH:32]>CO.C(OCC)(=O)C.[Pd]>[ClH:32].[OH:30][C:18]1([CH2:17][N:14]2[CH2:15][CH2:16][NH:11][CH2:12][C:13]2=[O:31])[CH2:19][CH2:20][N:21]([C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 234475964-Benzyloxycarbonyl-1-[4-hydroxy-1-(4-pyridyl)piperidin-4-ylmethyl]-2-oxo-1,2,3,4-tetrahydropyrazine

Product 1

HCID 234473171-[4-Hydroxy-1-(4-pyridyl)piperidin-4-ylmethy]-2-piperazinone Hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-benzyloxycarbonyl-1-[4-hydroxy-1-(4-pyridyl)piperidin-4-ylmethyl]-2-oxo-1,2,3,4-tetrahydropyrazine (6.93 g) in methanol (100 ml) were added 4N hydrochloric acid in ethyl acetate (4 ml) and 10% palladium on carbon (2.0 g), and the mixture was stirred, under hydrogen atmosphere, at room temperature for 15 hours. The catalyst was removed by filtration, and the filtrate was concentrated and dried under reduced pressure to give colorless syrup of the title compound (5.39 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-e99a71219958422e957f8eaa251db993
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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