Reacción #4318

Ecuación de reacción

N-[2-(phenylsulfonyl)ethyl]-2-propanamine

1,1'-carbonyldiimidazole

N-(3-aminopropyl)piperidine

→

oil

Rendimiento 27.1%

N-(1-Methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[3-(1-piperidinyl)propyl]urea

Rendimiento 27.1%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 20 hr
2. 2
   OtroThe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in a 60/40 mixture of ether and methylene chloride
4. 4
   ExtracciónThe solution was extracted with three portions of water
5. 5
   Secadowas dried over magnesium sulfate
6. 6
   OtroThe solvent was removed in vacuo
7. 7
   Otroto give an oil
8. 8
   LavadoFlash chromatography on silica gel (chloroform and methanol, gradiently eluted with methanol up to 10% methanol)

Procedimiento

A mixture of 5.16 g (0.0319 mole) of 1,1'-carbonyldiimidazole and 4.16 g (0.029 mole) of N-(3-aminopropyl)piperidine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 6.13 g (0.027 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 20 hr. The solvent was removed in vacuo, and the residue was dissolved in a 60/40 mixture of ether and methylene chloride, respectively. The solution was extracted with three portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (chloroform and methanol, gradiently eluted with methanol up to 10% methanol) gave 2.89 g (27.1%) of oil:

Fuente