Benzoyl chloride → N-(1,3-benzodioxol-5-ylmethyl)benzamide

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.

1. additionwas appropriately added
2. additionAfter adding dropwise
3. washthe dropping funnel was washed with tetrahydrofuran (10 mL)
4. stirringThe reaction mixture was stirred at 2-11° C. for 15 hr under a nitrogen atmosphere
5. customThe consumption of the starting material
6. additionTo the reaction mixture was added water (50 mL) at 11° C.
7. customThe organic layer was separated
8. extractionthe aqueous layer was extracted twice with ethyl acetate (44 mL)
9. washThe 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. dry with materialdried over magnesium sulfate (18 g)
11. customThe large part of the solvent was evaporated under reduced pressure at 35° C.
12. additionlower (content 61 g), and ethyl acetate (61 mL) was added to the residue
13. filtrationThe crystals were collected by filtration
14. washwashed with ethyl acetate (46 mL)
15. customdried under reduced pressure at 50° C.

ORDレコード

ord-859119f4d72a429d89d244a001747340

出典データセット

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08530506B2