3-Chloro-2-methyl-1-propene → N-[1-methyl-1-(3-chlorophenyl)ethyl]-2-methyl-2-propenylamine

HRID 1707232Notes

Reaction equation

HRID 1707232 reaction equation
[CH3:1][C:2]([NH2:11])([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[CH:5]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]([CH3:22])=[CH2:21]>CN(C)C=O>[CH3:3][C:2]([NH:11][CH2:21][C:20]([CH3:22])=[CH2:19])([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[CH:5]=1)[CH3:1]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 135695212-(3-Chlorophenyl)propan-2-amine

Product 1

HCID 18962886N-[1-methyl-1-(3-chlorophenyl)ethyl]-2-methyl-2-propenylamineYield 75.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To 15 ml of N,N-dimethylformamide were added 2.6 g of 1-methyl-1-(3-chlorophenyl)ethylamine, 2.0 g of potassium carbonate and 2.1 g of 3-chloro-2-methylpropene, and the solution was then stirred at 85° C. for 1 hour. After potassium carbonate was removed by filtration, 100 ml of water were added, followed by extraction with toluene. The resultant extract was dried over anhydrous sodium sulfate, and then concentrated by an evaporator. Afterward, silica gel column chromatography was done to obtain 2.6 g of the desired amine.

Workup

  1. customAfter potassium carbonate was removed by filtration, 100 ml of water
  2. additionwere added
  3. extractionfollowed by extraction with toluene
  4. extractionThe resultant extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated by an evaporator

Sources & evidence

ORD record
ord-ab2f67676f654b0a8d6aeb85dda35479
Source dataset
uspto-grants-1994_10
Patent number
US05352655

Reaction notes

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