Salicylaldehyde → 2-(((1-Benzylpiperidin-4-yl)amino)methyl)phenol

HRID 67063Notes

Reaction equation

HRID 67063 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BH4-].[Na+]>CO>[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][CH2:1][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])[CH2:19][CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 4158521-Benzyl-4-piperidylamineHCID 4311764Sodium borohydride

Product 1

HCID 47925042-(((1-Benzylpiperidin-4-yl)amino)methyl)phenolYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this reference example, 9.76 g of salicylaldehyde, 15.12 g of 1-benzyl-4-amino-piperidine and 100 ml of methanol are mixed and stirred at room temperature for one hour. While the resultant mixture is cooled with ice, 3.2 g of sodium borohydride is added thereto over a period of one hour and 30 minutes. Then, the mixture is stirred at room temperature for 2 hours. The resultant reaction mixture is poured into 1 l of ice water. The light yellow crystals deposited are separated by filtration and then dissolved in 200 ml of ethyl acetate. The ethyl acetate solution is washed with a saturated aqueous sodium chloride, dried and subsequently concentrated under reduced pressure to obtain 19.0 g of light yellow crystals. The crystals are recrystallized from ethanol to obtain 12.0 g of the desired product.

Workup

  1. additionis added
  2. waitover a period of one hour
  3. custom30 minutes
  4. stirringThen, the mixture is stirred at room temperature for 2 hours
  5. customThe resultant reaction mixture
  6. customThe light yellow crystals deposited are separated by filtration
  7. dissolutiondissolved in 200 ml of ethyl acetate
  8. washThe ethyl acetate solution is washed with a saturated aqueous sodium chloride
  9. customdried
  10. concentrationsubsequently concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea407051a732415e85d81bf46a8b64a6
Source dataset
uspto-grants-1982_08
Patent number
US04344945

Reaction notes

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