Reacción #80337

Ecuación de reacción

2-thiophenecarboxylic acid

N,N'-dicyclohexylcarbodiimide

1-hydroxybenzotriazole

4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenylamine

→

title compound

Rendimiento 73.0%

N-[4-(4-piperidinomethyl-2 -pyridyloxy)-cis-2-butenyl]thiophene-2-carboxamide

Rendimiento 73.0%

Disolventes

ethyl acetate

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe urea which precipitated
2. 2
   Otrowas removed by filtration
3. 3
   workup.ADDITIONThe filtrate was diluted with water
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate
6. 6
   Secadowith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
7. 7
   OtroThe solvent was then removed by distillation under reduced pressure
8. 8
   Otrothe residue was purified by column chromatography through silica gel
9. 9
   workup.ADDITIONby volume mixture of methanol and methylene chloride as the eluent

Procedimiento

240 mg of 2-thiophenecarboxylic acid, 390 mg of N,N'-dicyclohexylcarbodiimide and 275 mg of 1-hydroxybenzotriazole were added to a solution of 485 mg of 4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenylamine in 10 ml of dry dimethylformamide, and the resulting mixture was stirred at room temperature for 17 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate, and the urea which precipitated was removed by filtration. The filtrate was diluted with water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:19 by volume mixture of methanol and methylene chloride as the eluent, to give 499 mg (yield 73%) of the title compound as an oil.

Fuente