Diisopropylethylamine → (2.3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[3-(5-methoxy-1H-indol-3-yl)-propyl]-amine

HRID 1290257

反応式

HRID 1290257 の反応式
Cl.[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[CH2:12][NH2:13].[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH2:25][CH2:26][CH2:27]Br.C(N(C(C)C)CC)(C)C>CN(C=O)C>[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[CH2:12][NH:13][CH2:27][CH2:26][CH2:25][C:19]1[C:18]2[C:22](=[CH:23][CH:24]=[C:16]([O:15][CH3:14])[CH:17]=2)[NH:21][CH:20]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 28498361,4-Benzodioxan, 2-(aminomethyl)-, hydrochlorideHCID 18923869HCID 18923869、化合物

生成物 1

HCID 18923901(2.3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-[3-(5-methoxy-1H-indol-3-yl)-propyl]-amine収率 34%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

2,3-Dihydro-1,4-benzodioxin-2-methanamine hydrochloride (2.3 g, 11.0 mmole) in DMF (100 ml) was slowly added to a mixture of 5-methoxy-3-(3-bromopropyl)indole (3.0 g, 11.0 mmole) and diisopropylethylamine (9.7 ml, 55 mmole) in 100 ml of DMF with stirring and the mixture was heated at 80° C. for 24 hours. Most of DMF was removed in vacuum and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The dichloromethane solution was dried over anhydrous sodium sulfate, filtered, concentrated in vacuum and chromatographed on silica gel using ethyl acetate as the eluant. The combined fractions of free base of the expected product (1.3 g, 3.7 mmole, 34%) were concentrated, treated with 0.25M of fumaric acid in ethanol (8.1 ml, 2.0 mmole) and diluted first with 50 ml of ethanol-diethyl ether (1:1) and then with a minimum amount of hexane to precipitate the title compound as a white solid, (2:1) fumarate salt, m.p. 135°-136° C.

後処理

  1. customMost of DMF was removed in vacuum
  2. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  3. dry with materialThe dichloromethane solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel

出典と根拠

ORDレコード
ord-9ccc56ad12a2462daa5851204c59c692
出典データセット
uspto-grants-1998_05
特許番号
US05750724

関連ノート

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