Reacción #95499

Ecuación de reacción

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

potassium carbonate

cyanogen bromide

→

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

Disolventes

chloroform

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter heating
2. 2
   Temperaturaat reflux for 2.75 hours
3. 3
   Lavadothe cooled product is washed with 10% sodium hydroxide and water
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated
6. 6
   Otroto yield a crude solid which
7. 7
   Otrois chromatographed on silica gel (650 g)
8. 8
   Otrois then recrystallized from ether-dichloromethane

Procedimiento

A solution of 18.23 g of 1-(2-nitrophenyl)-1'-methylspiro[indoline-3,4'-piperidine] of Example 15 in 100 ml of chloroform is added dropwise over 50 minutes to a rapidly stirred slurry of 11.65 g of potassium carbonate and 8.94 g of cyanogen bromide in 100 ml of chloroform under nitrogen. After heating at reflux for 2.75 hours, the cooled product is washed with 10% sodium hydroxide and water, dried over anhydrous magnesium sulfate and concentrated to yield a crude solid which is chromatographed on silica gel (650 g) using ether-chloroform and is then recrystallized from ether-dichloromethane to yield a solid, mp 148°-150° C. of 1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine].

Fuente