150459-78-2

To a solution of 5,6,7,8-tetrahydro-1-quinoline (10 g, 67 mmol) in dichloromethane (134 mL) was added sequentially trimethylcyanosilane (TMSCN, 18.5 mL, 147.4 mmol) and dimethylcarbamoyl chloride (13.7 mL, 147.4 mmol) at room temperature. The reaction mixture was stirred overnight and then the reaction was quenched with 3M aqueous sodium hydroxide solution (350 mL). The mixture was stirred vigorously for 10 minutes, followed by multiple extractions with dichloromethane (200 mL x 6). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography to afford 5,6,7,8-tetrahydro-2-cyanoquinoline (6.5 g, 61% yield).ESI-MS (M + H+) = 159.

[1] Patent: WO2008/95058, 2008, A1. Location in patent: Page/Page column 18-19
[2] Patent: EP1424336, 2004, A1. Location in patent: Page 107
[3] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 5, p. 453 - 458
[4] Heterocycles, 2002, vol. 57, # 1, p. 111 - 122