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

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.

1. customthe urea which precipitated
2. customwas removed by filtration
3. additionThe filtrate was diluted with water
4. extractionextracted with ethyl acetate
5. washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate
6. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
7. customThe solvent was then removed by distillation under reduced pressure
8. customthe residue was purified by column chromatography through silica gel
9. additionby volume mixture of methanol and methylene chloride as the eluent

ORD record

ord-ec7f2c371ea540618a1ab27c4ee8a9de

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05616579