Water → 1-(3-Chloro-alpha,alpha-dimethylbenzylamino)-2-propanone

HRID 1461653Notes

Reaction equation

HRID 1461653 reaction equation
Cl[CH2:2][C:3](=[O:5])[CH3:4].[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([NH2:13])([CH3:12])[CH3:11].C(N(CC)CC)C.O>CN(C)C(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([NH:13][CH2:2][C:3](=[O:5])[CH3:4])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 8471TriethylamineHCID 135695212-(3-Chlorophenyl)propan-2-amine

Product 1

HCID 157541571-(3-Chloro-alpha,alpha-dimethylbenzylamino)-2-propanoneYield 30.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

27.8 g (0.3 mol) of chloroacetone, 16.0 g (0.1 mol) of 3-chloro-α,α-dimethylbenzylamine and 11.2 g (0.11 mol) of triethylamine were dissolved in 200 ml of N,N-dimethylacetamide, and the mixture was heated at 80° C. for 3 hours under stirring. The reaction solution was cooled, then poured into a large amount of water and extracted with toluene. The toluene layer was washed with water and then dried over anhydrous magensium sulfate. Then, the toluene layer was distilled off under reduced pressure to obtain 6.9 g (yield: 30.6%) of the desired compound.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracted with toluene
  3. washThe toluene layer was washed with water
  4. dry with materialdried over anhydrous magensium sulfate
  5. distillationThen, the toluene layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3eadc16ad36343afbfc43b7c4a09a4f1
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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