반응 #479348

반응 방정식

[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate

3-(5-fluoro-benzo[b]thiophen-3-yl)-propylamine

→

title compound

수율 63.6%

N-[3-(5-Fluoro-1-benzothien-3-yl)propyl]-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}amine

수율 63.6%

용매

sodium bicarbonate

dimethylsulfoxide

반응 조건

후처리

1. 1
   온도The reaction was then heated at 40° C. for two days
2. 2
   기타resulting in complete conversion
3. 3
   기타The cooled reaction
4. 4
   추출extracted with ethyl acetate (3×35 mL)
5. 5
   세척The combined organic layers were washed with brine (40 mL)
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacua

실험 절차

A mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (151 mg, 0.669 mmol) and 3-(5-fluoro-benzo[b]thiophen-3-yl)-propylamine (140 mg, 0.335 mmol) in anhydrous dimethylsulfoxide (7 mL) was stirred at ambient temperature for three days without any apparent reaction occurring. The reaction was then heated at 40° C. for two days, resulting in complete conversion. The cooled reaction was diluted with saturated aqueous sodium bicarbonate (35 mL) and extracted with ethyl acetate (3×35 mL). The combined organic layers were washed with brine (40 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacua. Flash chromatography on silica gel (2/2/96 methanol/2 M ammonia in methanol/methylene chloride) afforded 90 mg (63%) of the title compound as a yellow viscous oil, which was converted to its fumarate salt as a yellow solid: mp 117-120° C.; MS (ES) m/z 423 [M+H]+; [α]D −29.1° (c 0.94, DMSO)

출처