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

HRID 2254303

반응식

HRID 2254303 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bf0cc91449c54cfabc7513b4ef60cd7c
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05235055

연결된 노트

불러오는 중…