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

To a solution of 0.160 g (0.594 mmol) of 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-4-phenylbutan-1-one in 20 ml of acetic acid, 0.080 ml (0.88 mmol) of 50% aqueous dimethylamine and 0.072 ml (0.88 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 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 to ethyl acetate/methanol=4/1) 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 to ethyl acetate/methanol=4/1)

ORD record

ord-b8a66e8e970343379a9da532f08f65bb

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998433