1-Amino-2-propanol → HCID 4719394, compound

HRID 1608225Notes

Reaction equation

HRID 1608225 reaction equation
[NH2:1][CH2:2][CH:3]([CH3:5])[OH:4].[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO>[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][NH:1][CH2:2][CH:3]([CH3:5])[OH:4]

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 69962-ChlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 4719394HCID 4719394, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 2-amino-1-methylethanol (25.0 g), 2-chlorobenzaldehyde (51.5 g), sodium bicarbonate (33.6 g), and methanol (1000 ml) is refluxed with stirring for 4 hours. After the reaction mixture is cooled to 10° C., sodium borohydride (13.9 g) is added in small portions, and the resulting mixture is stirred at 25° C. for 1 hour. The solvent is removed under reduced pressure, and the residue is diluted with water and extracted with chloroform. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure to give the title compound (55.0 g) as an oil.

Workup

  1. temperatureis refluxed
  2. stirringthe resulting mixture is stirred at 25° C. for 1 hour
  3. customThe solvent is removed under reduced pressure
  4. additionthe residue is diluted with water
  5. extractionextracted with chloroform
  6. washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-6f9a80c21fa64730852d57c21e9dc754
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

Loading…