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

반응식

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH2:8].C([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])C.[CH2:16](O)[CH3:17]>>[N:11]1[CH:12]=[CH:13][C:16]([CH:17]2[C:3]3[CH:4]=[CH:5][S:1][C:2]=3[CH2:6][CH2:7][NH:8]2)=[CH:15][CH:14]=1

참가 물질

반응물 3

HCID 702Ethanol

HCID 8471Triethylamine

HCID 116521Thiopheneethanamine

생성물 1

HCID 212643794-(Pyridin-4-YL)-4,5,6,7-tetrahydrothieno[3,2-C]pyridine

실험 절차

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.