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

HRID 430066Notes

Reaction equation

HRID 430066 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:10]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:10][NH:1][CH2:2][CH2:3][CH2:4][OH:5]

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 90863-Amino-1-propanolHCID 11430Potassium Carbonate

Product 1

HCID 4183093-{[(3,4-Dichlorophenyl)methyl]amino}propan-1-olYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Aminopropanol (1.5 g, 20 mmol) was dissolved in dry DMF and treated with 3,4-dichlorobenzyl chloride (2.62 ml, 19 mmol) followed by anhydrous potassium carbonate (1.38 g, 10 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was partitioned between 1M HCl and dichloromethane, the layers separated and the aqueous phase washed with dichloromethane. The aqueous phase was adjusted to pH 12 with 1M NaOH, and extracted with dichloromethane. The organic extract was dried (MgSO4) and evaporated to afford the title compound as a colourless oil (0.96 g 22%); δH (CDCl3) 1.68-1.77 (2H, m), 2.87 (2H, t, J=5.7 Hz), 3.75 (2H, s), 3.80 (2H, t, J=5.3 Hz), 7.12-7.41 (3H, m); MS (ES+) 234 (5%, MH+), 159 (100).

Workup

  1. customThe mixture was partitioned between 1M HCl and dichloromethane
  2. customthe layers separated
  3. washthe aqueous phase washed with dichloromethane
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-a8132368aea54b3fa12376120c6d356b
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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