Hydrochloric Acid → HCID 67337162, compound

Temperature

85 °C

3-(5-Ammoniopentanoyl)pyridinium chloride (152 mg, 0.60 mmol) was suspended into ethanol (10 mL) in a reaction vessel and treated with concentrated hydrochloric acid (5 drops). Pyridine-3-carboxaldehyde (84 mg, 0.78 mmol) was added and the reaction vessel was sealed. The reaction was heated to 85° C. for 48 hours, then cooled to room temperature. The reaction mixture was concentrated under reduced pressure and treated with saturated NaHCO3(aq), then extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The recovered material was then eluted through a 20 gram column of silica gel with a 98:2:0.2 and 96:4:0.4 CH2Cl2:MeOH:NH4OH step gradient (500 mL each step). The recovered material was dissolved into MeOH and treated with 3 eq. of 6 N HCl(aq). This solution was concentrated under reduced pressure and the recovered material dissolved into hot isopropanol. This solution was allowed to cool to room temperature, then diluted with ether which produced a precipitate. The precipitate was recovered by vacuum filtration, washed with fresh isopropanol, then dried under vacuum giving 39 mg (18%) of a brown solid. LC-MS: RT=2.14 min, [M+H]+=250.1.

1. customthe reaction vessel was sealed
2. temperaturecooled to room temperature
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. additiontreated with saturated NaHCO3(aq)
5. extractionextracted three times with EtOAc
6. washThe EtOAc extracts were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. washThe recovered material was then eluted through a 20 gram column of silica gel with a 98:2:0.2 and 96:4:0.4 CH2Cl2
11. dissolutionThe recovered material was dissolved into MeOH
12. concentrationThis solution was concentrated under reduced pressure
13. dissolutionthe recovered material dissolved into hot isopropanol
14. temperatureto cool to room temperature
15. additiondiluted with ether which
16. customproduced a precipitate
17. filtrationThe precipitate was recovered by vacuum filtration
18. washwashed with fresh isopropanol
19. customdried under vacuum

ORD record

ord-1a0e00a9b1db4ae5990706cfc02b4f31

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662965B2