4-Chlorobenzaldehyde → [(6-Chloro(3-pyridyl)methyl][(4-chlorophenyl)methyl]amino}ethan-1-ol

Participants

Reaction Steps

This compound was prepared in a manner analogous to that set forth in Step A of Example 1, using 5.0 grams (0.0268 mole) of 2-{[(6-chloro-3-pyridyl)methyl]amino}ethan-1-ol (prepared in Step A of Example 1), 3.8 grams (0.0268 mole) of 4-chlorobenzaldehyde, 8.5 grams (0.040 mole) of sodium triacetoxyborohydride and 6.5 grams (0.053 mole) of magnesium sulfate in 100 mL of 1,2-dichloroethane. The crude product was purified with column chromatography on silica gel. Elution was accomplished using 2% methanol in methylene chloride as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 7.9 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence