[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:2]=1.Cl.O[NH3+:17].[OH-].[Na+].[Al]>C(O)C.[Ni]>[NH2:17][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:9][CH2:10]1
38.05 Grams of N-(3-pyridylmethyl)-4-piperidone and 27.8 grams of hydroxylammonium hydrochloride were dissolved in 600 milliliters of ethanol. 300 milliliters of 30% sodium hydroxide were added and the solution refluxed for half an hour, and then 40 grams of nickel, aluminium alloy were carefully added portionwise to the refluxing solution. The solution was refluxed for a further 3 hours, cooled and filtered through kieselguhr. The solution was evaporated and the residue treated with ether. The combined ether extracts were dried over magnesium sulphate and evaporated to give 33.72 grams of 4-amino-N-(3-pyridylmethyl)piperidine.
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