Pyridine → N-[(10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-yl)methyl]-4-pyridinamine

Participants

Reaction Steps

A solution of 4.7 grams (50 milliliters) of 4-aminopyridine in 50 c.c. of dry pyridine was treated dropwise at room temperature with a solution of 6.6 grams of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylcarbonyl chloride (M. A. Davis, Stanley O. Winthrop, J. Steward, F. A. Sunahara, and F. Herr, J. Medicin. Chem. 1963, 6, 251-5) in 50 c.c. of toluene. After the exothermic reaction subsided the mixture was stirred at room temperature for 4 hours and was then poured into 30 c.c. of water. 100 milliliters of toluene were added and the phases were separated. The toluene phase was washed once with 100 c.c. of water, then the combined aqueous phases were back-extracted with toluene (3×100 c.c.). The combined toluene solutions were dried (MgSO4) and evaporated, leaving an oily residue which was evaporated several times with further toluene and finally once with ethanol to remove residual pyridine, giving 8.45 grams of a yellow solid. This solid was crystallised from toluene (charcoal) giving off-white crystals (4.78 g. 61%), mp 145°-6°; second crop, off-white crystals (0.96 g, 12%), mp 145°-7.5°.

Provenance & Evidence