反应详情

To 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.

1. customthe ice-bath was removed
2. temperaturethe reaction mixture refluxed for six hours
3. customquenched (EtOAc and 10% NaOH)
4. customthe resulting granular precipitate removed by filtration
5. concentrationThe filtrate was concentrated to ca 20 ml
6. dissolutiondissolved in CHCl3
7. washwashed with H2O
8. customthe solvent removed
9. customto give a yellow-green oil
10. customthe solvent evaporated
11. customThe residue crystallized from CH2Cl2