反応 #4293

反応方程式

N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester

sodium hydroxide

methylene chloride

→

title compound

N-[2-[(4-Fluorophenyl)sulfonyl]ethyl]-2-propanamine hydrochloride

溶媒

HBr

methanol

反応条件

後処理

1. 1
   温度at reflux for 8 hr
2. 2
   温度The reaction mixture was cooled with ice
3. 3
   抽出The aqueous phase was extracted with chloroform
4. 4
   抽出The chloroform layer was extracted with sodium hydroxide
5. 5
   その他Evaporation of the chloroform layer
6. 6
   その他gave an oil residue
7. 7
   抽出the solution extracted with 1N sulfuric acid
8. 8
   workup.ADDITIONwith a mixture of ice and 50% sodium hydroxide solution
9. 9
   抽出extracted with chloroform
10. 10
    その他Removal of chloroform
11. 11
    その他gave an oil

実験手順

A solution of 60.25 g (0.165 mole) of N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)carbamic acid phenyl ester in 400 ml of 48% HBr was heated at reflux for 8 hr. The reaction mixture was cooled with ice and made alkaline with 50% sodium hydroxide. The aqueous phase was extracted with chloroform. The chloroform layer was extracted with sodium hydroxide. Evaporation of the chloroform layer gave an oil residue. The oil was dissolved in methylene chloride and the solution extracted with 1N sulfuric acid. The acidic layer was made alkaline with a mixture of ice and 50% sodium hydroxide solution and extracted with chloroform. Removal of chloroform gave an oil, the free base of the title compound, which was dissolved in methanol and reacted with ethereal hydrogen chloride to give the hydrochloride salt. On recrystallization from methanol-diethyl ether a white crystalline product; m.p. 168°-169° C. in 31.1% yield was obtained.

出典