2-Methoxy-2,4,6-cycloheptatrien-1-one → 2-(4-Methyl-1-piperazinyl)cycloheptimidazole

HRID 128080

반응식

HRID 128080 반응식
I.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9](=[NH:11])[NH2:10])[CH2:5][CH2:4]1.[Na].CO[C:15]1[C:16](=O)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1>C(O)C>[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:10]=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=[C:21]3[N:11]=2)[CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 165462-Methoxy-2,4,6-cycloheptatrien-1-oneHCID 5360545SodiumHCID 202843594-Methylpiperazine-1-carboximidamide hydroiodide

생성물 1

HCID 136531152-(4-Methyl-1-piperazinyl)cycloheptimidazole

시약·촉매·용매 1

HCID 702Ethanol용매3회

실험 절차

4-Methyl-1-piperazinecarboximidamide hydroiodide (17.8 g) was suspended in ethanol (15 ml). Sodium (1.5 g) in ethanol (47.8 ml) was added to it. The mixture was stirred at room temperature for 30 min. A solution of 2-methoxy-2,4,6-cycloheptatrien-1-one in ethanol (12 ml) was added dropwise. The mixture was refluxed for 3 hr and evaporated. The residue was taken in water and extracted with ethyl acetate in a continuous extractor. The organic layer was dried and evaporated. The residue was chromatographed through a column of silica gel using 5% methanol in chloroform and the eluates were evaporated. The residue was taken up in diethyl ether and filtered. The precipitate was crystallized from diethyl ether-hexane to obtain the title compound (3.4 g): mp 93°-95° C.; ir (CHCl3) 1600, 1565 and 1523 cm-1 ; uv max (MeOH) 291 (ε7,280), 262(ε28,445) and 238 nm(ε23,970); nmr-(CDCl3) δ 2.3(3H,s), 2.5(4H,t), 4.0(4H,t) and 7.2-8.0(5H,m) and Anal. Calcd for C13H16N4 : C, 68.39 % H, 7.06% N, 24.54% N, 24.54% and Found: C, 68.45% H, 6.99% N, 24.27%.

후처리

  1. temperatureThe mixture was refluxed for 3 hr
  2. customevaporated
  3. extractionextracted with ethyl acetate in a continuous extractor
  4. customThe organic layer was dried
  5. customevaporated
  6. customThe residue was chromatographed through a column of silica gel using 5% methanol in chloroform
  7. customthe eluates were evaporated
  8. filtrationfiltered
  9. customThe precipitate was crystallized from diethyl ether-hexane

출처 및 근거

ORD 기록
ord-b7c9e065a63b4d43a06a4f1bc4c19422
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04258188

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