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

HRID 1609457Notes

Reaction equation

HRID 1609457 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.[BH4-].[Na+]>C(O)C>[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 3

HCID 1013-HydroxybenzaldehydeHCID 8082PiperidineHCID 4311764Sodium borohydride

Product 1

HCID 8269741-(3-Hydroxybenzyl)piperidineYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 800 ml of ethanol was dissolved 122 g of 3-hydroxybenzaldehyde and thereto was gradually added 210 g of piperidine. To the mixture was added 38 g of sodium borohydride under cooling with ice and the mixture was stirred for 8 hours at room temperature. The resulting mixture was concentrated at a reduced pressure. To a residue were added ice-cold water and hydrochloric acid to render a solution acidic. The solution was washed with diethyl ether. An aqueous layer was made alkaline with addition of sodium carbonate and then extracted with ethyl acetate. After removing the solvent, 106 g (yield 55%) of 3-(1-piperidinomethyl)phenol was obtained in the form of white crystal.

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe resulting mixture was concentrated at a reduced pressure
  3. additionTo a residue were added ice-cold water and hydrochloric acid
  4. washThe solution was washed with diethyl ether
  5. additionwith addition of sodium carbonate
  6. extractionextracted with ethyl acetate
  7. customAfter removing the solvent

Sources & evidence

ORD record
ord-2f8a856fac894105b1de49b3d7882367
Source dataset
uspto-grants-1995_03
Patent number
US05401739

Reaction notes

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