(S)-1-(3-Benzyloxy-propyl)-3-methyl-piperazin-2-one → (S)-1-(3-Hydroxy-propyl)-3-methyl-piperazin-2-one

HRID 655527Notes

Reaction equation

HRID 655527 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[C:13]1=[O:19])C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[C:13]1=[O:19]

Participants

4

Reactant 1

HCID 66999230(S)-1-(3-Benzyloxy-propyl)-3-methyl-piperazin-2-one

Product 1

HCID 66999467(S)-1-(3-Hydroxy-propyl)-3-methyl-piperazin-2-oneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (S)-1-(3-benzyloxy-propyl)-3-methyl-piperazin-2-one (9.07 g, 34.6 mmol) in methanol (320 ml) was heated for 14 h at 70° C. under a hydrogen atmosphere (7 bar) in the presence of palladium (10% on activated charcoal, 7.36 g). After cooling, insoluble material was removed by filtration and the filtrate evaporated to produce the title compound (5.90 g, 99%). Colorless oil, MS (ISP)=173.1 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. custominsoluble material was removed by filtration
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-59f837b625d147ef989e202ad7923fcf
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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