3,4-Dichlorobenzyl chloride → 1-Propanol, 2-(3,4-dichlorobenzylamino)-2-methyl-

HRID 2211964Notes

Reaction equation

HRID 2211964 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][C:12]([CH3:16])([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][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14]

Participants

3

Reactant 2

HCID 76093,4-Dichlorobenzyl chlorideHCID 118072-Amino-2-methyl-1-propanol

Product 1

HCID 993601-Propanol, 2-(3,4-dichlorobenzylamino)-2-methyl-Yield 93.7%

Conditions

Temperature
60 °C

Procedure

3,4-Dichlorobenzyl chloride (3.95 g) was added to 2-amino-2-methylpropan-1-ol (17.8 g) and the mixture was stirred at 60° C. under nitrogen for 2 h. Excess amine was removed by distillation under vacuum and the residue was partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl acetate (100 ml). The phases were separated, the organic layer was washed with water (4×100 ml) and brine (100 ml), dried (Na2SO4) and concentrated under vacuum to give the title compound as a white solid (4.7 g).

Workup

  1. customExcess amine was removed by distillation under vacuum
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate (100 ml) and ethyl acetate (100 ml)
  3. customThe phases were separated
  4. washthe organic layer was washed with water (4×100 ml) and brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-25083806558c4368a5ee6f4c1648fc27
Source dataset
uspto-grants-2006_09
Patent number
US07101882B2

Reaction notes

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