Reaction #1023

Reaction equation

2-amino-1-propanol

sodium hydride

4-chloropyridine hydrochloride

→

desired product

Yield 30.2%

1-methyl-2-(4-pyridyloxy)ethylamine

Yield 30.2%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred for 20 hours at room temperature
2. 2
   OtherAfter completion of the reaction
3. 3
   Filtrationthe solids were filtered off
4. 4
   OtherThe solvent in the filtrate was removed under reduced pressure
5. 5
   OtherThe residue was purified by column chromatography on silica gel

Procedure

6.2 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 4.0 g of 60% sodium hydride and 50 mL of N,N-dimethylformamide at 5° C.-10° C. After the reaction mixture was stirred for 30 minutes, 12.5 g of 4-chloropyridine hydrochloride in limited amounts was added to the reaction mixture. The mixture was stirred for 20 hours at room temperature. After completion of the reaction, the solids were filtered off. The solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 3.8 g of the desired product (yield: 30%). Refractive index: 1.5469.

Source