4-Pyridinecarboxaldehyde → (+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine

HRID 9873

반응식

HRID 9873 반응식
[NH2:1][CH:2]1[CH2:10][CH:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[CH2:4][CH2:3]1.[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=O.S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[N:16]1[CH:17]=[CH:18][C:13]([CH:11]=[N:1][CH:2]2[CH2:10][CH:9]3[N:5]([CH2:6][CH2:7][CH2:8]3)[CH2:4][CH2:3]2)=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 133894-PyridinecarboxaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21988494Octahydroindolizin-7-amine

생성물 1

HCID 21988493(+/-)-7-(4-Pyridylmethyleneamino)-1,2,3,5,6,7,8,8a-octahydroindolizine수율 100.7%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

(±)-7-Amino-1,2,3,5,6,7,8,8a-octahydroindolizine (4.91 g (35.0 mmol), prepared as described in 1)) was dissolved in toluene (95 ml). To the solution were added 4-formylpyridine (3.34 ml, 35.0 mmol) and anhydrous magnesium sulfate (3.75 g, 31.2 mmol), and the resulting mixture was stirred at 70° C. for 3 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure, to give the title compound (8.08 g) as a pale yellow oil (yield quantitative).

후처리

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-48980c3bc29d442994e424cd77e71dc8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091352B2

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