Reacción #980456

Ecuación de reacción

hydrochloric acid

indolecarboxylic acid chloride

THF

n-BuLi

1-methyl-2-piperidinemethanol

THF

→

title compound

(1-Methyl-2-piperidyl)methyl 1H-indole-3-carboxylate

Disolventes

hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling for 30 min
2. 2
   workup.STIRRINGAfter stirring at room temperature for 5 hours
3. 3
   OtroThe organic layer was separated
4. 4
   Extracciónthe aqueous layer was extracted with EtOAc
5. 5
   Extracciónagain extracted with EtOAc
6. 6
   ExtracciónThe basic extract
7. 7
   Lavadowas washed successively with water and saturated aqueous sodium chloride
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroThe pale yellow crystals thus produced
11. 11
    Otrowere recrystallized from a chloroform-methanol mixture

Procedimiento

To a THF solution (17 ml) of 1-methyl-2-piperidinemethanol (1.70 g, 13.2 mmol) cooled in an ice-sodium chloride bath to -5° C. was dropwise added a 1.5M hexane solution of n-BuLi (8.7 ml, 13.0 mmol) over a period of 5 min. Stirring was continued under ice-cooling for 30 min. To a mixture was then dropwise added a THF solution (5 ml) of indolecarboxylic acid chloride (1.50 g, 8.35 mmol) over a period of 5 min. After stirring at room temperature for 5 hours, a reaction solution was poured onto diluted hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were then adjusted with saturated aqueous NaCO3 to a pH of >10 and again extracted with EtOAc. The basic extract was washed successively with water and saturated aqueous sodium chloride, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The pale yellow crystals thus produced were recrystallized from a chloroform-methanol mixture to give 1.20 g of the title compound as prisms. m.p. 168°-170° C.;

Fuente