Ethanol → 4-(Pyridin-4-yl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

2-(2-Thienyl)-ethylamine (2 g, 15.7 mmol) 4-pyridylaldehyde (1.68 g, 15.7 mmol), triethylamine (1 ml) and ethanol (15 ml) were mixed and the reaction mixture was stirred at room temperature for 15 hours, then evaporated in vacuo. The crude oil was added trifluoroacetic acid (75 m) at once (strongly exothermic reaction). The reaction mixture was stirred at room temperature for 0.5 hour, then evaporated in vacuo. The residue was dissolved in dichloromethane (150 ml) and washed with 2 N sodium hydroxide (100 ml). The aqueous phase was extracted with dichloromethane (3×50 ml). The combined organic phases were dried with MgSO4, filtered and evaporated in vacuo to give an oil (3.21 g) which was crystallised from a mixture of dichloromethane and hexane to afford 2.4 g (71%) of the title compound.

1. customevaporated in vacuo
2. additionThe crude oil was added trifluoroacetic acid (75 m) at once (
3. customstrongly exothermic reaction)
4. stirringThe reaction mixture was stirred at room temperature for 0.5 hour
5. customevaporated in vacuo
6. dissolutionThe residue was dissolved in dichloromethane (150 ml)
7. washwashed with 2 N sodium hydroxide (100 ml)
8. extractionThe aqueous phase was extracted with dichloromethane (3×50 ml)
9. dry with materialThe combined organic phases were dried with MgSO4
10. filtrationfiltered
11. customevaporated in vacuo

ORD record

ord-ba4366b94aeb419eb3d71f99303f6e27

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06177443B1