Phenethylamine → 5,6,7,8-Tetrahydro-5-[(2-phenylethyl)amino]-1-(2-propenyl)-2(1H)-quinolinone

HRID 1195170노트

반응식

HRID 1195170 반응식
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O=[C:11]1[CH2:20][CH2:19][CH2:18][C:17]2[N:16]([CH2:21][CH:22]=[CH2:23])[C:15](=[O:24])[CH:14]=[CH:13][C:12]1=2.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:3]1([CH2:2][CH2:1][NH:9][CH:11]2[CH2:20][CH2:19][CH2:18][C:17]3[N:16]([CH2:21][CH:22]=[CH2:23])[C:15](=[O:24])[CH:14]=[CH:13][C:12]2=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 1001PhenethylamineHCID 6101p-Toluenesulfonic acidHCID 103305125,6,7,8-tetrahydro-5-oxo-1-(2-propenyl)-2(1H)-quinolinone

생성물 1

HCID 184091115,6,7,8-Tetrahydro-5-[(2-phenylethyl)amino]-1-(2-propenyl)-2(1H)-quinolinone수율 89.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of phenethylamine (6.1 g), 5,6,7,8-tetrahydro-5-oxo-1-(2-propenyl)-2(1H)-quinolinone (10.0 g), and a catalytic amount of para-toluenesulfonic acid was heated in refluxing toluene (150 ml), with azeotropic removal of water, for 18 hrs. The solution was cooled and washed with water. The aqueous phase was extracted with dichloromethane, and the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. Sodium borohydride (1.8 g) was added to the residue in ethyl alcohol (150 ml) and the resulting mixture was stirred at room temperature for 0.5 hr. The mixture was concentrated in vacuo, and the residue was quenched with water. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was purified by high performance liquid chromatography (silica gel, eluted with methanol/ethyl acetate) to afford 13.6 g (89%) of product. Recrystallization from diethyl ether/petroleum ether provided the analytical sample, mp 60°-62° C.

후처리

  1. customwith azeotropic removal of water
  2. temperatureThe solution was cooled
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. additionSodium borohydride (1.8 g) was added to the residue in ethyl alcohol (150 ml)
  10. concentrationThe mixture was concentrated in vacuo
  11. customthe residue was quenched with water
  12. extractionThe mixture was extracted with ethyl acetate
  13. washThe combined organic layers were washed with brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. filtrationfiltered
  16. concentrationthe filtrate was concentrated
  17. customThe residue was purified by high performance liquid chromatography (silica gel, eluted with methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-cc5445119d924e5e84adc30b87f69915
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110815

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