Triethylamine → 3-Piperidin-1-ylpyridine-2-carbonitrile

A mixture of 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl 1′-oxide (1.30 g, 7.30 mmol), trimethylsilyl cyanide (1.45 g, 14.6 mmol) and triethyl amine (1.47 g, 14.6 mmol) in dry CH3CN (25 mL) was heated at reflux for 16 h, yielding a red solution. The reaction mixture was then cooled to room temperature, and saturated aqueous NaHCO3 (20 mL) was added. After concentrated under reduced pressure the mixture was extracted with CH2Cl2 (4×30 mL). The extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (CH2Cl2) to afford 3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-2′-carbonitrile as a pale yellow solid (1.26 g, 92%). 1H NMR (CDCl3) δ 1.58-1.66 (m, 2H), 1.75-1.83 (m, 4H), 3.21 (t, 4H, J=5.7 Hz), 7.34-7.38 (m, 2H), 8.19-8.22 (m, 1H).

1. temperaturewas heated
2. temperatureat reflux for 16 h
3. customyielding a red solution
4. concentrationAfter concentrated under reduced pressure the mixture
5. extractionwas extracted with CH2Cl2 (4×30 mL)
6. dry with materialdried over anhydrous Na2SO4
7. filtrationAfter filtration the solvent
8. customwas removed by evaporation under vacuum
9. customthe residue was purified by flash chromatography on a silica gel column (CH2Cl2)

ORD record

ord-cc176b2d724f44a190832feaf1173964

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07291631B2