Dimethylamine → N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-3-oxo-1-propanamine

HRID 1014355노트

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HRID 1014355 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].[CH3:20][NH:21][CH3:22]>CO>[CH3:20][N:21]([CH3:22])[CH2:3][CH2:2][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]

참가 물질

4

반응물 2

HCID 674DimethylamineHCID 594417802-Acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 59441847N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-3-oxo-1-propanamine수율 71%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
65 °C

실험 절차

A solution of 2-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (0.8 g, 3 mmol) in methanol (10 mL) was treated with dimethyl amine (10 mL, 2 M in THF, 20 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 20% methanol/dichloromethane) to give N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1 H)-isoquinolinyl]-3-oxo-1-propanamine (0.65 g, 71%). ESIMS (M+H)+=308.

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 20% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-252c0847ab7340e696541b276f506630
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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