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

HRID 1371401Notes

Reaction equation

HRID 1371401 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-fc91a1e74e0f49db8cc2e334f08fcc05
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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