C(C1C=CC=CN=1)=C.C(OC(=O)C)(=O)C.[C-]#N.[K+].C([O-])([O-])=O.[Na+].[Na+].[C:25]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)#[N:26]>O.CCO.[Ni]>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][CH2:27][CH2:25][NH2:26]
2-Vinyl pyridine (105 g) and acetic anhydride (204 g) were combined at room temperature, and a solution of KCN (130 g) in 250 ml of water was added dropwise to the stirring solution. The rate of addition was adjusted to maintain a gentle reflux. After the addition was complete, the mixture was refluxed for 22 h, and the pH of the solution then adjusted to 8 with aqueous Na2CO3 solution. The mixture was extracted with DCM (600 ml), the extracts dried over MgSO4 and then evaporated to a brown oil. The oil was then vacuum distilled at approximately 0.6 mmHg pressure. The product distilled over as a clear oil at 100-107° C. in 56% yield. The oil of 2-(2-cyanoethyl)-pyridine (200 mg, 1.5 mmol) was taken up in 6 ml of EtOH and treated with 2 ml of 0.88NH3 solution and 50 mg of RaNi. The mixture was hydrogenated at 30 psi H2 pressure for 16 h, and was then filtered and evaporated to give the title product (ca. 200 mg) which was used with no further purification.
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