N-Methylbenzylamine → N-methyl-1-phenyl-N-[(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]methanamine

HRID 2063824노트

반응식

HRID 2063824 반응식
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O.I[CH2:23][C:24]1([CH3:36])[CH2:28][C:27]2[C:29]([CH3:35])=[CH:30][C:31]([CH3:34])=[C:32]([CH3:33])[C:26]=2[O:25]1>C(OCC)(=O)C.O>[CH3:1][N:2]([CH2:23][C:24]1([CH3:36])[CH2:28][C:27]2[C:29]([CH3:35])=[CH:30][C:31]([CH3:34])=[C:32]([CH3:33])[C:26]=2[O:25]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 152683052-(Iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran

생성물 1

HCID 66760229N-methyl-1-phenyl-N-[(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]methanamine수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

N-methylbenzylamine (766 mg, 3.16 mmol) and potassium carbonate (1.09 g, 7.90 mmol) were added to a solution of DMA (5 mL) containing 2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran (1.00 g, 3.16 mmol) synthesized in Reference Example 126, and the mixture was stirred under heated reflux for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added thereto to separate an organic layer. The organic layer was washed with water and saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-93:7) to give 730 mg of the title compound (yield: 75%).

후처리

  1. customsynthesized in Reference Example 126
  2. temperatureunder heated
  3. temperaturereflux for 4 hours
  4. customto separate an organic layer
  5. washThe organic layer was washed with water and saturated saline
  6. customdried
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-93:7)

출처 및 근거

ORD 기록
ord-8c4d5d476906495d815bd295bbc14b3b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288390B2

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