反应 #95504

反应方程式

ethyl chloroformate

1-(2-aminophenyl)-1'-methylspiro[indoline-3,4'-piperidine]dihydrochloride

triethanolamine

ethyl chloroformate

→

1-[2-(ethoxycarbonyl)aminophenyl]-1'-methylspiro[indoline-3,4'-piperidine]

溶剂

chloroform

chloroform

反应条件

后处理

1. 1
   温度The resulting mixture is cooled in an ice bath
2. 2
   workup.WAITto stand 16 hours
3. 3
   洗涤The product is washed thrice with water, brine
4. 4
   干燥dried over anhydrous sodium sulfate
5. 5
   浓缩concentrated
6. 6
   其他to give a crude carbamate
7. 7
   其他affords an oil
8. 8
   其他The material crystallizes on prolonged standing

实验过程

A slurry of 10.36 g of 1-(2-aminophenyl)-1'-methylspiro[indoline-3,4'-piperidine]dihydrochloride of Example 1b in 60 ml of chloroform is treated portionwise with 12.3 ml of triethanolamine. The resulting mixture is cooled in an ice bath and treated dropwise over 40 minutes with a solution of 2.7 ml of ethyl chloroformate in 20 ml of chloroform. After stirring at room temperature for 1 hour, an additional 3.0 ml of ethyl chloroformate is added and the mixture is permitted to stand 16 hours. The product is washed thrice with water, brine, dried over anhydrous sodium sulfate, concentrated and pumped on under high vacuum to give a crude carbamate. Chromatography on silica gel (100 g) using ether-methylene chloride affords an oil. The material crystallizes on prolonged standing to yield 1-[2-(ethoxycarbonyl)aminophenyl]-1'-methylspiro[indoline-3,4'-piperidine], mp 99.5°-101.0° C.

来源