Diisopropylethylamine → N-[3-(Quinolin-5-yloxy)propyl]-2,3-dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine

HRID 2254303

反応式

HRID 2254303 の反応式
[CH2:1]1[O:15][C:14]2[C:3](=[CH:4][C:5]3[O:10][CH2:9][CH:8]([CH2:11][NH2:12])[O:7][C:6]=3[CH:13]=2)[O:2]1.Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH:23]=[CH:24][CH:25]=[N:26]2.C(N(C(C)C)CC)(C)C>CN(C=O)C>[N:26]1[C:27]2[C:22](=[C:21]([O:20][CH2:19][CH2:18][CH2:17][NH:12][CH2:11][CH:8]3[O:7][C:6]4[CH:13]=[C:14]5[O:15][CH2:1][O:2][C:3]5=[CH:4][C:5]=4[O:10][CH2:9]3)[CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 197450172,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamineHCID 200790485-(3-Bromopropoxy)quinoline

生成物 1

HCID 19745013N-[3-(Quinolin-5-yloxy)propyl]-2,3-dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine収率 38.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine (2.3 g, 11 mmole), 5-(3-bromopropoxy)quinoline (2.54 g, 9.2 mmole), and diisopropylethylamine (2.6 g, 20 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 250 g of silica gel using 2% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the residue (2.0 g) recrystallized from 50 ml of ethanol with the addition of 6 ml of 4N isopropanolic HCl to give 1.4 g of the title compound as an orange solid dihydrochloride, one-quarter hydrate, m.p. 140°-145° C.

後処理

  1. customThe solvent was then removed in vacuum
  2. washThe mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on 250 g of silica gel using 2% methanol/dichloromethane as eluant
  7. concentrationconcentrated in vacuum
  8. customthe residue (2.0 g) recrystallized from 50 ml of ethanol with the addition of 6 ml of 4N isopropanolic HCl

出典と根拠

ORDレコード
ord-bf0cc91449c54cfabc7513b4ef60cd7c
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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