3-Hydroxybenzaldehyde → 1-(3-Hydroxybenzyl)piperidine

HRID 325688Notes

Reaction equation

HRID 325688 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(O)C.[Pd]>[N:10]1([CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][CH:7]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 8082Piperidine

Product 1

HCID 8269741-(3-Hydroxybenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Hydroxybenzaldehyde (15 g) and piperidine (15 ml) in ethanol (500 ml) were hydrogenated over 10% palladium/carbon catalyst. The catalyst was removed by filtration and the solvent was evaporated off. The residue was triturated with light petroleum (b.p. 60°-80°) and the resulting solid was recrystallised from acetonitrile to give the title compound as a buff coloured solid (8.7 g) m.p. 134°-7°. TLC silica, methanol, Rf 0.56.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated off
  3. customThe residue was triturated with light petroleum (b.p. 60°-80°)
  4. customthe resulting solid was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-cbbd7bf905644c86be863064567b8d04
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Reaction notes

Loading…