Diisopropylethylamine → 7-[3-[(7-Hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)amino]propoxy]chromen-4-one

HRID 5573

반응식

HRID 5573 반응식
Cl.[OH: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]([C:24](=[O:30])[CH:25]=[CH:26][O:27]2)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH:9]([CH2:12][NH:13][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:29]=[C:28]4[C:23]([C:24](=[O:30])[CH:25]=[CH:26][O:27]4)=[CH:22][CH:21]=3)[O:8][C:7]=2[CH:14]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 189238902,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine hydrochlorideHCID 197967547-(3-Bromopropoxy)chromen-4-one

생성물 1

HCID 197967627-[3-[(7-Hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)amino]propoxy]chromen-4-one수율 10.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine hydrochloride (4.7 g, 22 mmole), 7-(3-bromopropoxy)chromen-4-one (6.1 g, 22 mmole) and diisopropylethylamine (18.8 ml, 108 mmole) were combined in 200 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. The residue was chromatographed on a silica gel column using first dichloromethane and then 5% methanol/dichloromethane as eluents. The fractions containing material with Rf=0.37 on silica gel tlc (chloroform/methanol/ammonia=95/5/1) were combined, concentrated, and the residual solid was recrystallized from ethanol with the addition of 4N isopropanolic HCl and ether to give 0.85 g of title compound as a light brown solid hydrochloride, quarter hydrate, m.p. 186°-189° C.

후처리

  1. customThe solvent was then removed
  2. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue was chromatographed on a silica gel column
  7. additionThe fractions containing material with Rf=0.37 on silica gel tlc (chloroform/methanol/ammonia=95/5/1)
  8. concentrationconcentrated
  9. customthe residual solid was recrystallized from ethanol with the addition of 4N isopropanolic HCl and ether

출처 및 근거

ORD 기록
ord-b5f1118b8c30426bbd0a88c29f75d946
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245051

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