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

HRID 35591Notes

Reaction equation

HRID 35591 reaction equation
[BH4-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>C(O)C.O>[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4311764Sodium borohydride

Product 1

HCID 8269741-(3-Hydroxybenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (1.52 g) was added to a stirred solution of 3-hydroxybenzaldehyde (4.9 g) and piperidine (6.8 g) in ethanol (25 ml) cooled in an ice-water bath. The mixture was stirred at ambient temperature for 16 hours and then poured into water (250 ml) and the resulting mixture acidified with 2N hydrochloric acid. The acidified mixture was extracted with ethyl acetate and the aqueous phase was made alkaline by the addition of aqueous ammonia solution (S.G. 0.880) to yield N-3-hydroxybenzylpiperidine (m.p. 135°-139° C.) as a colourless solid.

Workup

  1. temperaturecooled in an ice-water bath
  2. extractionThe acidified mixture was extracted with ethyl acetate
  3. additionby the addition of aqueous ammonia solution (S.G. 0.880)

Sources & evidence

ORD record
ord-89f7153ba59246a183e586c34cf69726
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Reaction notes

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