Hydrazine hydrate (1:1) → 4-(Hydroxymethyl)piperidin-3-ol

HRID 344289Notes

Reaction equation

HRID 344289 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH:10]([OH:16])[CH2:9]1)C1C=CC=CC=1.O.NN>C(O)C.[C].[Pd]>[OH:16][CH:10]1[CH:11]([CH2:14][OH:15])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 221357071-Benzyl-4-(hydroxymethyl)piperidin-3-ol

Product 1

HCID 222436184-(Hydroxymethyl)piperidin-3-olYield 107.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-benzyl-3-hydroxy-4-hydroxymethylpiperidine (7.1 g) and hydrazine monohydrate (1.56 ml) in ethanol was added 10% palladium carbon (3 g), and the resulting mixture was stirred at refluxing temperature for 5 hr. 10% Palladium carbon was filtered off and the solvent was evaporated under reduced pressure to give 4.51 g of 3-hydroxy-4-hydroxymethylpiperidine.

Workup

  1. temperatureat refluxing temperature for 5 hr
  2. filtration10% Palladium carbon was filtered off
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e88aadbd183547e09ce9734d83a4ac2e
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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