[H-].[Na+].[Na].COC([CH2:8][CH2:9][N:10]([CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:11][CH2:12][C:13]([O:15]C)=O)=O.Cl>C1C=CC=CC=1>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][N:10]2[CH2:9][CH2:8][C:13](=[O:15])[CH2:12][CH2:11]2)[CH:19]=172 Grams of sodium hydride (50% dispersion in oil) were added to 1.5 liters of sodium dried benzene and the suspension formed was refluxed. 137.61 grams of 3-[N,N-di(2-methoxycarbonylethyl)aminomethyl]pyridine were added dropwise to the refluxing sodium hydride suspension in benzene and the solution was heated for a further 21/2 hours. 500 Milliliters of concentrated hydrochloric acid was added carefully. The mixture was filtered, separated and the acid layer combined with a further 200 milliliters of concentrated hydrochloric acid and refluxed for 18 hours. Solid sodium carbonate was added till the solution had a pH of 8. The mixture was filtered and the solution treated with benzene. The benzene extracts were combined, dried over magnesium sulphate and the solvent was evaporated to give 66.58 grams of N-(3-pyridylmethyl)-4-piperidone.
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