Methylamine → (1H-indol-7-ylmethyl)(methyl)amine

HRID 1749757

반응식

HRID 1749757 반응식
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)=O.[CH3:12][NH2:13].[BH4-].[Na+]>CO>[NH:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:1][NH:13][CH3:12])[CH:8]=[CH:9]1

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 2734629Indole-7-carboxaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 59340341(1H-indol-7-ylmethyl)(methyl)amine수율 89%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of 7-formyl-1H-indole (0.23 g, 1.6 mmol) in methanol (10 mL) was added with a 40% solution of methylamine in methanol (0.6 mL, 6.4 mmol), and the mixture was stirred at room temperature for 1 hour. Then, the mixture was added portionwise with sodium borohydride (0.060 g, 4.8 mmol), and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, then the residue was added with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (99:1→95:5)) to obtain 1-(1H-indole-7-yl)-N-methylmethanamine (0.23 g, 89%).

후처리

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was added with ethyl acetate
  4. washthe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (99:1→95:5))

출처 및 근거

ORD 기록
ord-8e8493c2f9fc45f1a7ce5f6c5cfcebd2
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156827B2

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