3-(2-Pyrrolidinyl)pyridine synthesis
- Product Name:3-(2-Pyrrolidinyl)pyridine
- CAS Number:5746-86-1
- Molecular formula:C9H12N2
- Molecular Weight:148.21
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Yield:5746-86-1 84.7%
Reaction Conditions:
with hydrogen;palladium 10% on activated carbon in methanol for 5 h;
Steps:
1.D
D. Preparation of Nornicotine: Myosmine (32 g, 0.219 mol) was dissolved in 150 ml of methanol and hydrogenated at atmospheric pressure with 1.3 g of 10% palladium on carbon as catalyst. After 5 hours the mixture was filtered and the filtrate was concentrated to get a brown solid (32 g, 94.9% purity by GC). It was further purified by vacuum distillation at 0.1 mm Hg to get pure nornicotine (27.46 g, 84.7% yield, 97.5% purity by GC). 1H NMR (CDCl3): δ 1.66-2.72 (2H,m), 3.0 (2H,m), 4.13 (1H,t), 7.24 (1H,m), 7.69 (1H, dt), 8.46 (1H,dd), and 8.59 (1H,d). 13C-NMR (CDCl3): δ 148.4, 148.1, 140.16, 134.1, 123.3, 60.0, 46.8, 34.2, and 25.4. IR: 3291, 2960, 1641, 1578 Cm-1.
References:
Divi's Laboratories Limited EP2487172, 2012, A1 Location in patent:Page/Page column 4
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