反应详情

Add 1-chloroethylchloroformate (0.58 mL, 5.38 mmol) to a stirred solution of [3-(benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-benzyl-methyl-amine (0.9619 g, 2.62 mmol) and 1,2-dichloroethane (25 mL). Heat the reaction to reflux under nitrogen for 1.5 hours. Add methanol (30 mL) and heat the reaction at reflux for 30 minutes. Cool the reaction to room temperature and make it basic using 2M ammonia in methanol. Concentrate on a rotary evaporator to give the crude product. Purify the crude product by flash chromatography on silica gel eluting with 0.5% concentrated ammonium hydroxide/5% ethanol/chloroform to yield 0.6303 g (87%) of [3-(benzo[b]thiophen-4-yloxy)-5-methyl-hexyl]-methyl-amine: mass spectrum (ion spray) m/z=278.2(M+1); HPLC (90/5/5 to 0/95/5 water/acetonitrile/5% formic acid in water) XTerra MS C18 2.1 mm×50 mm×3.5 micron: Retention time: 2.52 minutes, Purity: >99.9%.

1. temperatureHeat
2. customthe reaction
3. temperatureto reflux under nitrogen for 1.5 hours
4. customthe reaction
5. temperatureat reflux for 30 minutes
6. temperatureCool
7. customthe reaction to room temperature
8. concentrationConcentrate on a rotary evaporator
9. customto give the crude product
10. customPurify the crude product by flash chromatography on silica gel eluting with 0.5% concentrated ammonium hydroxide/5% ethanol/chloroform