Dimethylamine → 1-(2-dimethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-2-(2-naphthoxy)ethan-1-one

To a solution of 0.230 g (0.748 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-2-(2-naphthoxy)ethan-1-one in 20 ml of acetic acid, 0.10 ml (1.1 mmol) of 50% aqueous dimethylamine and 0.092 ml (1.1 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 45 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=9/1 to 6/1) to yield the desired product.

1. distillationAfter the solvent was distilled off under reduced pressure
2. extractionextracted with dichloromethane 2 times
3. washThe combined organic layer was washed with water
4. dry with materialdried over anhydrous sodium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=9/1 to 6/1)

ORD record

ord-57f0d85399504cd2afbb48674c85dcc6

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998433