Reaction #7015

Reaction equation

amine

[4-Benzyl-5-(3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-4H-[1,2,4]triazol-3-ylmethyl]-(2-methoxy-ethyl)-amine

formaldehyde

sodium triacetoxyborohydride

→

title compound

[4-Benzyl-5-(3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-4H-[1,2,4]triazol-3-ylmethyl]-(2-methoxy-ethyl)-methyl-amine

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe reaction mixture was partitioned between dichloromethane and aqueous sodium carbonate solution
2. 2
   Otherthe layers separated
3. 3
   DryingThe organic phase was dried (MgSO4)
4. 4
   Otherevaporated under reduced pressure
5. 5
   Otherthe product triturated from ether

Procedure

The amine from example 43 (50 mg, 0.12 mmol), formaldehyde (37% aq, 40 μl, 0.49 mmol) and sodium triacetoxyborohydride (51 mg, 0.24 mmol) in dichloromethane (1 ml) was stirred vigorously at room temperature for 21 hours. The reaction mixture was partitioned between dichloromethane and aqueous sodium carbonate solution, and the layers separated. The organic phase was dried (MgSO4), evaporated under reduced pressure, and the product triturated from ether to afford the title compound as a white solid.

Source