2-Aminopropanol → 2-{[(3,4-Dichlorophenyl)methyl]amino}propan-1-ol

HRID 227447Notes

Reaction equation

HRID 227447 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Cl.[NH2:11][CH:12]([CH3:15])[CH2:13][OH:14]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:11][CH:12]([CH3:15])[CH2:13][OH:14]

Participants

3

Reactant 2

HCID 51262-AminopropanolHCID 76093,4-Dichlorobenzyl chloride

Product 1

HCID 219629772-{[(3,4-Dichlorophenyl)methyl]amino}propan-1-olYield 79%

Conditions

Temperature
50 °C

Procedure

3,4-Dichlorobenzyl chloride (0.988 g) was added to 2-amino-1-propanol (4.10 g) and the mixture was stirred at 50° C. under nitrogen for 2 h. The mixture was partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl acetate (100 ml) and the phases were separated. The organic layer was washed with water (4×100 ml) and brine, dried (Na2SO4) then concentrated under vacuum to give the title compound as a white solid (0.935 g).

Workup

  1. customThe mixture was partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl acetate (100 ml)
  2. customthe phases were separated
  3. washThe organic layer was washed with water (4×100 ml) and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-13bf7408a42746339d1d1f6832df3e06
Source dataset
uspto-grants-2009_07
Patent number
US07560548B2

Reaction notes

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