Morpholine → 6-(Methyloxy)-2-[3-(4-morpholinyl)propanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1014357노트

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HRID 1014357 반응식
[C:1]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[C:10]([O:15][CH3:16])[CH:11]=2)[CH2:6]1)(=[O:4])[CH:2]=[CH2:3].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CO>[CH3:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[N+:17]([O-:19])=[O:18])[CH2:6][N:5]([C:1](=[O:4])[CH2:2][CH2:3][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[CH2:14][CH2:13]2

참가 물질

4

반응물 2

HCID 8083MorpholineHCID 594417802-Acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 594418816-(Methyloxy)-2-[3-(4-morpholinyl)propanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
65 °C

실험 절차

A solution of 2-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (425 mg, 1.62 mmol) in methanol (5 mL) was treated with morpholine (1.00 mL, 11.5 mmol, Aldrich) and heated at 65° C. in a sealed tube for 16 h. The mixture was cooled, concentrated, and partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic layer was separated, dried over magnesium sulfate, filtered, and purified by chromatography on SiO2 (dichloromethane to 25% methanol/dichloromethane) to give 6-(methyloxy)-2-[3-(4-morpholinyl)propanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline. This material was taken directly to the next step without a determination of yield. 1H NMR (400 MHz, DMSO-d6) is complicated by amide rotomers δ ppm 2.32-2.41 (m, 4 H), 2.52-2.62 (m, 4 H), 2.79-2.97 (two app triplets at 2.83 and 2.94, 2 H), 3.48-3.58 (m, 4 H), 3.63-3.72 (m, 2 H), 3.89 (s, 3 H), 4.55-4.69 (two singlets at 4.57 and 4.67, 2 H), 7.18-7.21 (m, 1 H), 7.80 (s, 1 H); ESIMS (M+H)+=350.

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompartitioned between ethyl acetate and saturated aqueous ammonium chloride
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. custompurified by chromatography on SiO2 (dichloromethane to 25% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-7374614c416049fa8a2ceed1cd7aa726
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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