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

Temperature

100 °C

To a solution of 0.503 g (1.548 mmol) of 1-(5,7-dihydro-4H-thieno[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 0.17 g (1.9 mmol) of 50% aqueous dimethylamine and 0.15 g (1.9 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 3 hours. Additionally, 0.5 g (5.5 mmol) of 50% aqueous dimethylamine and 0.5 g (6.2 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 6 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium 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. stirringby stirring at 100° C. for 6 hours
2. distillationAfter the solvent was distilled off under reduced pressure
3. extractionextracted with dichloromethane 3 times
4. dry with materialThe combined organic layer was dried over anhydrous magnesium 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-2258d4cbb40641798b8b175825c9cdcc

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998433