Reaktion #70071

Reaktionsgleichung

benzoyl chloride

piperonylamine

triethylamine

→

N-benzoylpiperonylamine

Ausbeute 84.7%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas appropriately added
2. 2
   workup.ADDITIONAfter adding dropwise
3. 3
   Waschenthe 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
   SonstigeThe consumption of the starting material
6. 6
   workup.ADDITIONTo the reaction mixture was added water (50 mL) at 11° C.
7. 7
   SonstigeThe organic layer was separated
8. 8
   Extraktionthe aqueous layer was extracted twice with ethyl acetate (44 mL)
9. 9
   WaschenThe 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
    Trocknendried over magnesium sulfate (18 g)
11. 11
    SonstigeThe 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
    FiltrationThe crystals were collected by filtration
14. 14
    Waschenwashed with ethyl acetate (46 mL)
15. 15
    Sonstigedried under reduced pressure at 50° C.

Vorschrift

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.

Quelle