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

HRID 2186135Notes

Reaction equation

HRID 2186135 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-abb73e585a7b489f8c9abf907dce7e4d
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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