Hydrochloric Acid → HCID 66732297, compound

Methyl 2-(5-tert-butylthiophen-2-yl)isonicotinate (2.02 g, 7.34 mmol) was dissolved in hydrogen chloride (1.25 M in MeOH, 11.74 mL, 14.67 mmol) and stirred at room temperature for 30 min. The solvent was evaporated in vacuo. The residue was dissolved in MeOH (20 mL), platinum(IV) oxide (0.050 g, 0.22 mmol) added and the reaction mixture hydrogenated in a Büchi hydrogenator at 5 bar and room temperature for 3 h. Additional platinum(IV) oxide (0.050 g, 0.22 mmol) was added and the hydrogenation continued for 3 h. The reaction mixture was filtered through celite, washed with MeOH and the filtrate evaporated in vacuo. The residue was redissolved in MeOH (15 mL) and platinum(IV) oxide (0.167 g, 0.73 mmol) added. Hydrogenation was continued for 3 h. Additional platinum(IV) oxide (0.167 g, 0.73 mmol) was added and the hydrogenation continued for 2 h. The reaction mixture was filtered through celite, washed with MeOH and the filtrate evaporated in vacuo to yield methyl 2-(5-tert-butylthiophen-2-yl)piperidine-4-carboxylate hydrochloride (2.360 g, 101%) as a black oil. MS m/z 282 (M+H)+

1. customThe solvent was evaporated in vacuo
2. dissolutionThe residue was dissolved in MeOH (20 mL)
3. waitthe reaction mixture hydrogenated in a Büchi hydrogenator at 5 bar and room temperature for 3 h
4. waitthe hydrogenation continued for 3 h
5. filtrationThe reaction mixture was filtered through celite
6. washwashed with MeOH
7. customthe filtrate evaporated in vacuo
8. dissolutionThe residue was redissolved in MeOH (15 mL)
9. waitHydrogenation was continued for 3 h
10. waitthe hydrogenation continued for 2 h
11. filtrationThe reaction mixture was filtered through celite
12. washwashed with MeOH
13. customthe filtrate evaporated in vacuo

ORD record

ord-0b1575e58c3b481b86a12d9378c21c86

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415378B2