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

HRID 1034431Notes

Reaction equation

HRID 1034431 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.B([O-])([O-])O.[Na+].[Na+]>CO>[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 14496929Boric acid (H3BO3), disodium salt

Product 1

HCID 8269741-(3-Hydroxybenzyl)piperidineYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxybenzaldehyde (III) (0.246 mol, 30 g) was dissolved into 150 ml of methanol. Piperidine (IV) (0.6 mol, 52 g) was added to the solution and the mixture was stirred at room temperature to dissolution. To the solution was added under ice cooling sodium hydrogen borate (0.247 mol, 9.4 g) while stirring over 1 hour, followed by continued stirring for 1 hour at room temperature. The reaction mixture was concentrated under vacuum. The residue was dissolved in 200 ml of 3N hydrochloric acid and washed twice with 50 ml of ethyl acetate. The water layer was alkalinized (pH 10) with about 50 ml of concentrated aqueous ammonia to deposit crystals. The crystals were collected by filtration, washed with water, dried under vacuum, and recrystallized from a mixed solvent of acetone and n-hexane, to obtain 40 g of 3-piperidinomethylphenol (V) (yield: 84.7%). m.p. 135°-138° C.

Workup

  1. additionTo the solution was added under ice
  2. stirringwhile stirring over 1 hour
  3. stirringby continued stirring for 1 hour at room temperature
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. dissolutionThe residue was dissolved in 200 ml of 3N hydrochloric acid
  6. washwashed twice with 50 ml of ethyl acetate
  7. filtrationThe crystals were collected by filtration
  8. washwashed with water
  9. customdried under vacuum
  10. customrecrystallized from a mixed solvent of acetone and n-hexane

Sources & evidence

ORD record
ord-a5d0e33bec5c4f7e9d41c668ec775573
Source dataset
uspto-grants-1994_05
Patent number
US05317026

Reaction notes

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