Isopropylamine → HCID 14855249, compound

HRID 615614Notes

Reaction equation

HRID 615614 reaction equation
BrCCC1C([Cl:10])=C(Cl)C=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[C:14]=1CCBr.[CH:24]([NH2:27])([CH3:26])[CH3:25]>C(Cl)(Cl)Cl>[ClH:10].[Cl:20][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[Cl:19])[O:12][CH2:5][CH2:6][NH:27][CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 57302858HCID 57302858, compound

Product 1

HCID 14855249HCID 14855249, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 36.18 g. (0.135 mole) of 2-bromoethyl-3,4-dichlorophenyl ether and 31.8 g (0.54 mole) of isopropyl amine in 200 ml of chloroform was heated at reflux for 72 hours. Solvent was removed in a rotary evaporator and the residue partitioned between water and chloroform. The chloroform layer was extracted with 1N sulfuric acid. The aqueous phase, which contained a dispersed white solid, was made alkaline with 10% aqueous sodium hydroxide solution and extracted with chloroform. The chloroform layer was concentrated under vacuum to an oil, the free base. A portion of the oil was dissolved in methanol and treated with ethereal hydrogen chloride. The precipitate was recrystallized from methanol-diethyl ether. Overall yield of white crystalline product was 62.4% of theory based on the proportion taken. The melting point was 186°-187° C.

Workup

  1. temperatureat reflux for 72 hours
  2. customSolvent was removed in a rotary evaporator
  3. customthe residue partitioned between water and chloroform
  4. extractionThe chloroform layer was extracted with 1N sulfuric acid
  5. extractionextracted with chloroform
  6. concentrationThe chloroform layer was concentrated under vacuum to an oil
  7. dissolutionA portion of the oil was dissolved in methanol
  8. additiontreated with ethereal hydrogen chloride
  9. customThe precipitate was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-fd837758ef59415cb76ca20423d10375
Source dataset
uspto-grants-1985_02
Patent number
US04500529

Reaction notes

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