Reacción #70071

Ecuación de reacción

benzoyl chloride

piperonylamine

triethylamine

→

N-benzoylpiperonylamine

Rendimiento 84.7%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas appropriately added
2. 2
   workup.ADDITIONAfter adding dropwise
3. 3
   Lavadothe dropping funnel was washed with tetrahydrofuran (10 mL)
4. 4
   workup.STIRRINGThe reaction mixture was stirred at 2-11° C. for 15 hr under a nitrogen atmosphere
5. 5
   OtroThe consumption of the starting material
6. 6
   workup.ADDITIONTo the reaction mixture was added water (50 mL) at 11° C.
7. 7
   OtroThe organic layer was separated
8. 8
   Extracciónthe aqueous layer was extracted twice with ethyl acetate (44 mL)
9. 9
   LavadoThe combined organic layers were washed successively with 10% hydrochloric acid (40 mL), saturated aqueous sodium hydrogen carbonate solution (40 mL), water (40 mL) and saturated brine (44 mL)
10. 10
    Secadodried over magnesium sulfate (18 g)
11. 11
    OtroThe large part of the solvent was evaporated under reduced pressure at 35° C.
12. 12
    workup.ADDITIONlower (content 61 g), and ethyl acetate (61 mL) was added to the residue
13. 13
    FiltraciónThe crystals were collected by filtration
14. 14
    Lavadowashed with ethyl acetate (46 mL)
15. 15
    Otrodried under reduced pressure at 50° C.

Procedimiento

To a mixture of piperonylamine (20.0 g, 0.133 mol), tetrahydrofuran (87.5 mL) and triethylamine (13.9 g, 0.137 mol) was added dropwise benzoyl chloride (18.6 g, 0.133 mol), at −10-+6° C., and during dropwise addition, tetrahydrofuran (total 123 mL) was appropriately added thereto to stir the content. After adding dropwise, the dropping funnel was washed with tetrahydrofuran (10 mL). The reaction mixture was stirred at 2-11° C. for 15 hr under a nitrogen atmosphere. The consumption of the starting material was confirmed by TLC (eluent: hexane/ethyl acetate 1:1)). To the reaction mixture was added water (50 mL) at 11° C., and then added ethyl acetate (128 mL). The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate (44 mL). The combined organic layers were washed successively with 10% hydrochloric acid (40 mL), saturated aqueous sodium hydrogen carbonate solution (40 mL), water (40 mL) and saturated brine (44 mL), and dried over magnesium sulfate (18 g). The large part of the solvent was evaporated under reduced pressure at 35° C. or lower (content 61 g), and ethyl acetate (61 mL) was added to the residue. The crystals were collected by filtration, washed with ethyl acetate (46 mL), and dried under reduced pressure at 50° C. or lower to give N-benzoylpiperonylamine (28.6 g, 84.7%) as white crystals.

Fuente