Reacción #95497

Ecuación de reacción

6-chloro-1'-methyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

cyanogen bromide

potassium carbonate

→

6-chloro-1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThereafter, the mixture is sequentially quenched with water
2. 2
   Extracciónextracted with dilute sodium hydroxide
3. 3
   Otrodried
4. 4
   OtroThe chloroform is removed under reduced pressure
5. 5
   Otroproviding an orange oil which
6. 6
   Otrocrystallizes
7. 7
   OtroThe solid is recrystallized from an acetone-hexane mixture

Procedimiento

A mixture of 3.2 g of 6-chloro-1'-methyl-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine], Example 30, 2.0 g of cyanogen bromide and 6.0 g of potassium carbonate in 100 ml of chloroform is stirred at ambient temperature for 6 hours. Thereafter, the mixture is sequentially quenched with water, extracted with dilute sodium hydroxide and dried. The chloroform is removed under reduced pressure and the residue is passed through a silica gel column, ether eluant, providing an orange oil which crystallizes upon standing. The solid is recrystallized from an acetone-hexane mixture to provide orange prisms, mp 163°-165° C. of 6-chloro-1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine].

Fuente