反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH:9]([CH2:12][NH2:13])[O:8][C:7]=2[CH:14]=1.Br[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[N:27]1[C:28]2[C:23](=[CH:22][CH:21]=[C:20]([O:19][CH2:18][CH2:17][CH2:16][NH:13][CH2:12][CH:9]3[O:8][C:7]4[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[O:11][CH2:10]3)[CH:29]=2)[CH:24]=[CH:25][CH:26]=1参加物
反応条件
- 温度
- 80 °C
実験手順
2,3-Dihydro-7-methoxy-1,4-benzodioxin-2-methanamine (2.7 g, 14 mmole), 7-(3-bromopropoxy)quinoline (3.86 g, 14 mmole), and diisopropylethylamine (6.5 g, 50 mmole) were combined in 100 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with 500 ml of dichloromethane. The mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on 200 g of silica gel using 4% methanolchloroform as eluant. The product-containing fractions were combined and concentrated in vacuum and the residue recrystallized from 50 ml of ethanol with the addition of 8 ml of 4N isopropanolic HCl to give 1.5 g of the title compound as a yellow solid dihydrochloride monohydrate, m.p. 135°-142° C.
後処理
- customThe solvent was then removed in vacuum
- washThe mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuum
- customchromatographed on 200 g of silica gel using 4% methanolchloroform as eluant
- concentrationconcentrated in vacuum
- customthe residue recrystallized from 50 ml of ethanol with the addition of 8 ml of 4N isopropanolic HCl
出典と根拠
- ORDレコード
- ord-7c29aeda047b4dbfaa7fff4ccc26da3b
- 出典データセット
- uspto-grants-1993_08
- 特許番号
- US05235055
関連ノート
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