Benzoyl chloride → N-benzoyl-2-methoxybenzylamine

온도

16 °C

To a mixture of o-methoxybenzylamine (20.0 g, 0.146 mol), tetrahydrofuran (124 mL) and triethylamine (15.6 g, 0.154 mol) was added dropwise benzoyl chloride (20.5 g, 0.146 mol) at −9-0° C., and the dropping funnel was washed with THF (10 mL). Under a nitrogen atmosphere, the reaction mixture was gradually warmed to about 16° C. During warming, THF (total 51 ml) was appropriately added to stir the content. The reaction was confirmed by TLC (eluent: hexane/ethyl acetate (1:1)). The reaction mixture was stirred at about 16° C. for 10 hr, and cooled to 5° C. Water (44 ml) was added thereto, and the mixture was extracted three times with ethyl acetate (120 mL, 40 mL, 40 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 (20 g), and the solvent was evaporated under reduced pressure at 40° C. or lower. Ethyl acetate was added to the residue (content 74 g), and the solid was dissolved with heating to 60° C. The solution was gradually cooled to 6° C., the precipitated crystals were collected by filtration, washed with cold ethyl acetate (10 mL), and dried under reduced pressure at 40° C. or lower to give N-benzoyl-2-methoxybenzylamine (30.7 g, 87.1%) as white crystals.

1. washthe dropping funnel was washed with THF (10 mL)
2. temperatureDuring warming
3. additionTHF (total 51 ml) was appropriately added
4. stirringThe reaction mixture was stirred at about 16° C. for 10 hr
5. temperaturecooled to 5° C
6. additionWater (44 ml) was added
7. extractionthe mixture was extracted three times with ethyl acetate (120 mL, 40 mL, 40 mL)
8. 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)
9. dry with materialdried over magnesium sulfate (20 g)
10. customthe solvent was evaporated under reduced pressure at 40° C.
11. additionEthyl acetate was added to the residue (content 74 g)
12. dissolutionthe solid was dissolved
13. temperaturewith heating to 60° C
14. temperatureThe solution was gradually cooled to 6° C.
15. filtrationthe precipitated crystals were collected by filtration
16. washwashed with cold ethyl acetate (10 mL)
17. customdried under reduced pressure at 40° C.

ORD 기록

ord-5eaa3039d0ae455aab0c3b071588571a

출처 데이터셋

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08530506B2