Arecoline Hydrobromide → Norarecoline Hydrochloride

Temperatur

57.5 °C

Arecoline hydrobromide (25 g, 106 mmol) was neutralized with sodium carbonate (12.8 g, 120 mmol, 1.1 eq) in water (200 mL) for 30 min. The neutralized product was dissolved in toluene (50 mL) and added dropwise to a solution of triphosgene (16.3 g, 54.9 mmol, 0.52 eq) in toluene (100 mL) at 0° C. The resulting mixture was heated at 55-60° C. overnight. The reaction mixture was then concentrated in vacuo and the residue was dissolved in water (300 mL) and heated at 80° C. for 3 h. The water was evaporated and chased with toluene 3 times. The crude methyl 1,2,5,6-tetrahydropyridine-3-carboxylate hydrochloride, obtained as a thick brown oil, was used as is in the next reaction.

1. concentrationThe reaction mixture was then concentrated in vacuo
2. dissolutionthe residue was dissolved in water (300 mL)
3. temperatureheated at 80° C. for 3 h
4. customThe water was evaporated

ORD-Eintrag

ord-b979d331efa04ccaabbbfed0ec26ddd5

Quelldatensatz

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07595327B2