Sodium Bicarbonate → N-[3-(Quinolin-7-yloxy)propyl]-2,3-dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine
反応式
O.Cl.Cl.[N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH:20]3[O:25][C:24]4[CH:26]=[C:27]([O:30]C)[CH:28]=[CH:29][C:23]=4[O:22][CH2:21]3)[CH:12]=2)[CH:7]=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+]>Br>[N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][NH:18][CH2:19][CH:20]3[O:25][C:24]4[CH:26]=[C:27]([OH:30])[CH:28]=[CH:29][C:23]=4[O:22][CH2:21]3)[CH:12]=2)[CH:7]=[CH:6][CH:5]=1参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
N-[3-(Quinolin-7-yloxy)propyl]-2,3-dihydro-7-methoxy-1,4-benzodioxin-2-methanamine dihydrochloride monohydrate (0.94 g, 2.0 mmole), prepared above in Example 4, was dissolved in 10 ml of 48% HBr and refluxed for 24 hours under a nitrogen atmosphere. Upon cooling, the mixture was poured into 100 ml of saturated sodium bicarbonate solution to which 50 g of ice had been added. When the ice had melted, the mixture was extracted three times with 150 ml portions of 3:1 dichloromethane-isopropanol, the extracts dried over sodium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on 50 g of silica gel with 3% methanol/chloroform and the product-containing fractions were combined and concentrated in vacuum. The crude free base thus obtained was crystallized from 50 ml of ethanol with the addition of 3 ml of 4N isopropanolic HCl to give 0.5 g of the title compound as a yellow dihydrochloride monohydrate, m.p. 245°-246° C.