Potassium Carbonate → HCID 20079712, compound

HRID 1654159Notes

Reaction equation

HRID 1654159 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20]([CH3:23])[CH2:21][Cl:22]>CN(C)C=O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][N:2]([CH2:19][CH:20]([CH3:23])[CH2:21][Cl:22])[CH3:1])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 135897732-(4-Chlorophenyl)-N-methylethan-1-amine

Product 1

HCID 20079712HCID 20079712, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.9 g (0.1 mol) of N-methyl-2-(4-chlorophenyl)ethylamine were dissolved in 30 ml of dimethylformamide and treated with 20.7 g (0.3 mol) of anhydrous potassium carbonate. The mixture was stirred at 5° and treated with 12.6 ml (0.11 mol) of 1-bromo-2-methyl-3-chloropropane, whereupon the mixture was stirred at 30° for a further 4 hours, the solvent was evaporated at 30° under reduced pressure and the residue was treated with water. The separated oil was extracted three times with ether. The organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. The residual oil was distilled at 135°-140°/260 Pa, whereby there was obtained rac-4-chloro-N-(3-chloro-2-methylpropyl)-N-methylphenethylamine as a colourless oil which was used directly in the next step. MS: 260 (M)+.

Workup

  1. stirringwas stirred at 30° for a further 4 hours
  2. customthe solvent was evaporated at 30° under reduced pressure
  3. additionthe residue was treated with water
  4. extractionThe separated oil was extracted three times with ether
  5. dry with materialThe organic extracts were dried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. distillationThe residual oil was distilled at 135°-140°/260 Pa

Sources & evidence

ORD record
ord-3ccab5c8439e49d68700f4398631b8a7
Source dataset
uspto-grants-1995_04
Patent number
US05405866

Reaction notes

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