[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([CH2:13][CH2:14][C:15]([NH2:17])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C1COCC1.CO>[N:7]1([CH2:13][CH2:14][CH2:15][NH2:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1To an ice-cooled suspension of LiAlH4 (10.31 g, 0.27 mole) in THF (100 ml), a solution of 1-piperidine-propanamide, 4-(diphenylmethylene) 29.01 g, 0.091 mole) in THF (100 ml) was added dropwise. After stirring for 0.5 hours, the ice-bath was removed, the reaction mixture refluxed for six hours, quenched (EtOAc and 10% NaOH) and the resulting granular precipitate removed by filtration. The filtrate was concentrated to ca 20 ml, dissolved in CHCl3, washed with H2O, and the solvent removed to give a yellow-green oil. This was dissolved in MeOH, treated with HCl gas and the solvent evaporated. The residue crystallized from CH2Cl2 --Et2O to give 1-piperidinepropaneamine, 4-(diphenylmethylene)dihydrochloride hemihydrate as white solid in quantitative yield; mp 249°-252° C.
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