Reacción #4322

Ecuación de reacción

1-(3-aminopropyl)-4-methylpiperazine

1,1'-carbonyldiimidazole

maleic acid

N-(2-phenylsulfonylethyl)-2-propanamine

→

white crystalline solid

Rendimiento 68.8%

N-(1-Methylethyl)-N'-[3-(4-methyl-1-piperazinyl)propyl]-N-[2-(phenylsulfonyl)ethyl]urea maleate

Rendimiento 68.8%

Disolventes

tetrahydrofuran

methanol

methanol

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 16 hr
2. 2
   OtroThe solvent was removed in vacuo
3. 3
   Otrothe residue was partitioned between methylene chloride and water
4. 4
   SecadoThe solution was dried over magnesium sulfate
5. 5
   Otrothe solvent was removed in vacuo
6. 6
   Otroto give an oil
7. 7
   Otroa white solid precipitated
8. 8
   OtroThis was collected

Procedimiento

A mixture of 6.00 g (0.035 mole) of 1-(3-aminopropyl)-4-methylpiperazine and 6.97 g (0.043 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.17 g (0.036 mole) of N-(2-phenylsulfonylethyl)-2-propanamine in 100 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and water. The solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. The oil was dissolved in methanol; a solution of two equivalents of maleic acid in methanol was added, and a white solid precipitated. This was collected to give 15.48 g (68.8%) of white crystalline solid; m.p. 162°-163° C. with decomposition.

Fuente