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

HRID 847746Notes

Reaction equation

HRID 847746 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].[OH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O>C(O)C>[N:1]1([CH2:13][C:12]2[CH:11]=[C:10]([OH:9])[CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 8082PiperidineHCID 4311764Sodium borohydride

Product 1

HCID 8269741-(3-Hydroxybenzyl)piperidineYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine (26 g) and 4.7 g of sodium borohydride were added to a solution of 15 g of 3-hydroxybenzaldehyde in 100 ml of ethanol, and the mixture was stirred until a complete solution formed. The solution was allowed to stand overnight at room temperature. Under reduced pressure, the solvent was distilled off, and 200 ml of ice water was added to the residue. The mixture was acidified with hydrochloric acid, and allowed to stand for 1 hour. The raw material was extracted away using ethyl acetate, and the aqueous solution was separated. The aqueous layer was alkalized with aqueous ammonia, and the precipitated oily product was extracted with ethyl acetate. The solvent was distilled off, and the residue was recrystallized from acetone/n-hexane to afford 17.5 g of 3-(1-piperidinylmethyl)phenol.

Workup

  1. customformed
  2. distillationUnder reduced pressure, the solvent was distilled off
  3. addition200 ml of ice water was added to the residue
  4. waitto stand for 1 hour
  5. extractionThe raw material was extracted away using ethyl acetate
  6. customthe aqueous solution was separated
  7. extractionthe precipitated oily product was extracted with ethyl acetate
  8. distillationThe solvent was distilled off
  9. customthe residue was recrystallized from acetone/n-hexane

Sources & evidence

ORD record
ord-1ba48d1bcb0f4bfb829b23d2dc5cc2d0
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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