Triethylamine → 2-Ethoxycarbonylaminopropiophenone

HRID 2290371Notes

Reaction equation

HRID 2290371 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([CH3:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)(Cl)Cl>[CH2:24]([O:23][C:21]([NH:9][CH:10]([CH3:19])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2046302-Amino-1-phenylpropan-1-one;hydrochloride

Product 1

HCID 132935642-EthoxycarbonylaminopropiophenoneYield 73.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A solution of triethylamine (15 g) in chloroform (15 ml) was added dropwise to a stirred mixture of 2-aminopropiophenone hydrochloride (12 g) and chloroform (65 ml) at ice bath temperature in 10 minutes. To the stirred mixture was added dropwise a solution of ethyl chloroformate (8 g) in chloroform (20 ml) under the same conditions and then stirring was continued for 4 hours at ice bath temperature. The solution was evaporated under reduced pressure and the residue was dissolved in a mixture of ethyl acetate and water. The organic layer was separated, washed successively with a saturated aqueous solution of sodium bicarbonate, water, 5% hydrochloric acid, and water, dried over magnesium sulfate, and evaporated under reduced pressure to give an oil containing the object compound. The above obtained product was purified by column chromatography on silica gel (200 g) using a mixture of diisopropyl ether and chloroform (1:4) as an eluent to give an oil of 2-ethoxycarbonylaminopropiophenone (10.48 g).

Workup

  1. customThe solution was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed successively with a saturated aqueous solution of sodium bicarbonate, water, 5% hydrochloric acid, and water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. additioncontaining the object compound
  9. customThe above obtained product
  10. customwas purified by column chromatography on silica gel (200 g)
  11. additiona mixture of diisopropyl ether and chloroform (1:4) as an eluent

Sources & evidence

ORD record
ord-6ea7e453acb04301a659e5642e7ccf4f
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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