Potassium Carbonate → N1-(4-Methoxybenzyl)-3-(3-methoxyphenyl)-N7,N7-dimethylisoquinoline-1,7-diamine

HRID 1878640노트

반응식

HRID 1878640 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[N:3]=1.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N:12]([CH3:14])[CH3:13])[CH:10]=3)[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[N:3]=2)=[CH:27][CH:26]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 78357864HCID 78357864, 화합물

생성물 1

HCID 69298933N1-(4-Methoxybenzyl)-3-(3-methoxyphenyl)-N7,N7-dimethylisoquinoline-1,7-diamine수율 47%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-chloroimine isoquinoline II (500 mg, 1.6 mmol), 4-methoxy benzylamine (877 mg, 6.4 mmol), and potassium carbonate (2 g, 15 mmol) in DMF was refluxed overnight. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with water, dried, and concentrated. The residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (3:1) to afford compound III (310 mg, 47%). 1H NMR (300 MHz, CDCl3) δ: 7.74-7.62 (m, 3H), 7.45-7.33 (m, 4H), 7.22 (m, 1H), 6.92 (m, 3H), 6.66 (m, 1H), 5.24 (s, 1H), 4.91 (d, 2H), 3.91 (s, 3H), 3.85 (s, 3H), 3.09 (s, 6H).

후처리

  1. temperaturewas refluxed overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel with n-hexane-ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-2a8a3ccf837c4bafa7e7c27798240244
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314123B2

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