Epichlorohydrin → n-[1-(4-Chlorophenyl)-1-methylethyl]-2,3-epoxypropylamine

HRID 1956839Notes

Reaction equation

HRID 1956839 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH2:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([NH:16][CH2:1][CH:3]2[O:5][CH2:4]2)([CH3:14])[CH3:15])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 110302561-(4-Chlorophenyl)-1-methylethylamine

Product 1

HCID 18349585n-[1-(4-Chlorophenyl)-1-methylethyl]-2,3-epoxypropylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Epichlorohydrin (8.05 ml) was added dropwise to a solution of 1-(4-chlorophenyl)-1-methylethylamine (17.38 g) in methanol (17.5 ml) at 0° C. with stirring. The solution was warmed to ambient temperature and stirred for 48 hours. Sodium hydroxide solution (50%) (17.5 ml) was added and the mixture stirred for 15 minutes. The product was extracted with ether to give an oil which was purified by flash column chromatography on silica using petroleum ether, b.p. 40°-60° C./ethyl acetate/triethylamine (8:2:1) as the mobile phase with gradually increasing amounts of ethyl acetate to give N-[1-(4-chlorophenyl)-1-methylethyl]-2,3-epoxypropylamine as an oil.

Workup

  1. stirringstirred for 48 hours
  2. stirringthe mixture stirred for 15 minutes
  3. extractionThe product was extracted with ether
  4. customto give an oil which
  5. customwas purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-dd426a93900b46a0a72f97e37175e71c
Source dataset
uspto-grants-1998_07
Patent number
US05780642

Reaction notes

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