Reaction #1869160

Reaction equation

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

Yield 52.0%

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturethe resulting solution is heated
2. 2
   Temperatureto reflux for 48 hours
3. 3
   ConcentrationThe reaction mixture is concentrated at reduced pressure
4. 4
   Otherthe residue obtained
5. 5
   Otheris purified by chromatography over silica gel

Procedure

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.

Source