Reaction #7281

Reaction equation

4-hydroxymethyl-benzaldehyde

2-aminopyridine

acetic acid

sodium triacetoxyborohydride

→

title compound

Yield 74.0%

[4-(Pyridin-2-ylaminomethyl)-phenyl]-methanol

Yield 74.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherone hour at 50° C., followed by purification of crude material

Procedure

Using general procedure B: Reaction of 4-hydroxymethyl-benzaldehyde (1.01 g, 7.42 mmol), 2-aminopyridine (697 mg, 7.42 mmol), acetic acid (0.5 mL) and sodium triacetoxyborohydride (3.2 g, 14.8 mmol) in THF (20 mL) at room temperature under N2 for 40 min., then one hour at 50° C., followed by purification of crude material using chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2), afforded the title compound (1.17 g, 74%) as white foam.

Source