Reacción #1869160

Ecuación de reacción

1-methyl-4-piperidone

sodium methoxide

N-[1H-indol-5-yl]naphthalene-1-sulphonamide

→

N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide

Rendimiento 52.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting solution is heated
2. 2
   Temperaturato reflux for 48 hours
3. 3
   ConcentraciónThe reaction mixture is concentrated at reduced pressure
4. 4
   Otrothe residue obtained
5. 5
   Otrois purified by chromatography over silica gel

Procedimiento

To a solution of 712 mg (13.2 mMol) of sodium methoxide in 100 ml of methanol are added 850 mg (2.64 mMol) of N-[1H-indol-5-yl]naphthalene-1-sulphonamide followed by 596 mg (5.28 mMol) of 1-methyl-4-piperidone and the resulting solution is heated to reflux for 48 hours. The reaction mixture is concentrated at reduced pressure and the residue obtained is purified by chromatography over silica gel, using as eluent mixtures of methylene chloride/methanol/ammonia, to yield 573 mg (52%) of N-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]naphthalene-1-sulphonamide as a solid with m.p.=244-245° C.

Fuente