Benzaldehyde → 3-(Benzylamino)propanol

HRID 1050296Notes

Reaction equation

HRID 1050296 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+]>CO>[CH2:6]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 90863-Amino-1-propanolHCID 4311764Sodium borohydride

Product 1

HCID 784483-(Benzylamino)propanolYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-aminopropan-1-ol (3 g, 39.9 mmol) and benzaldehyde (4.05 mL, 39.9 mmol) in methanol (200 mL) was stirred at room temperature overnight. The solution was cooled to 0° C., and sodium borohydride (1.813 g, 47.9 mmol) was added slowly in several portions. The resulting mixture was stirred at room temperature for three hours, and then it was partitioned between water and dichloromethane (3x). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as an oil (6.5 g, 98%).

Workup

  1. customit was partitioned between water and dichloromethane (3x)
  2. dry with materialdried over Na2SO4
  3. customthe drying agent was removed by filtration
  4. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-b9f00ac8eb1d417cba739e7462d488e6
Source dataset
uspto-grants-2016_07
Patent number
US09382258B2

Reaction notes

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