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Water → 1,2,3,4-Tetrahydro-1,1,2-trimethyl-7-isoquinolinamine

HRID 650953
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HRID 650953 반응식
[I-].[NH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N+:9]([CH3:14])=[C:10]2[CH3:13])=[CH:5][CH:4]=1.[CH3:15][Mg]Cl.O>C1COCC1>[NH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:14])[C:10]2([CH3:15])[CH3:13])=[CH:5][CH:4]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 10946564HCID 10946564, 화합물HCID 178418332HCID 178418332, 화합물

생성물 1

HCID 109978251,2,3,4-Tetrahydro-1,1,2-trimethyl-7-isoquinolinamine수율 8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

7-Amino-1,2-dimethyl-3,4-dihydroisoquinolinium iodide (1.44 g, 4.8 mmol) was suspended in THF (200 ml), cooled to −78° C. and treated with methyl magnesium chloride (10 ml of a 3M solution in THF) added as a single portion. The reaction was allowed to reach room temperature over 18 h and poured into water (200 ml). The organic solvent was removed in vacuo and the resultant oily residue extracted into dichloromethane (3×50 ml). Evaporation in vacuo and chromatography through silica gel eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2) yielded the title compound as a yellow oil (0.07 g, 8%). For ease of handling the product was converted into a monohydrochloride.

후처리

  1. additionadded as a single portion
  2. customThe organic solvent was removed in vacuo
  3. extractionthe resultant oily residue extracted into dichloromethane (3×50 ml)
  4. customEvaporation in vacuo and chromatography through silica gel eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2)

출처 및 근거

ORD 기록
ord-f53df890d267462b9a67445e90af45f4
출처 데이터셋
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06277861B1

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