Réaction #53942

Équation de réaction

Huenig's base

4-(Trifluoromethyl)benzenesulfonyl chloride

trans-5-(4-Methylamino-cyclohexyl)-pentanoic acid diethylamide. hydrochloride

Huenig's base

4-(Trifluoromethyl)benzenesulfonyl chloride

→

trans-5-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyl}-pentanoic acid diethylamide

Rendement 85.5%

Solvants

CH2Cl2

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirring
2. 2
   AutreThe mixture was partitioned between CH2Cl2
3. 3
   LavageThe organic phase was washed with water, 1M KHSO4 and brine
4. 4
   Séchagedried over Na2SO4
5. 5
   Autreevaporated

Mode opératoire

0.8 g (2.6 mmol) trans-5-(4-Methylamino-cyclohexyl)-pentanoic acid diethylamide. hydrochloride in 20 ml CH2Cl2 was treated with 1.1 ml (6.3 mmol, 2.4 eq) Huenig's base, 706 mg (2.9 mmol, 1.1 eq) 4-(Trifluoromethyl)benzenesulfonyl chloride in 10 ml CH2Cl2 and 32 mg (0.26 mmol, 0.1 eq) DMAP. The solution was stirred at RT over night. Additonal 1.1 ml (6.3 mmol) Huenig's base, 706 mg (2.9 mmol) 4-(Trifluoromethyl)benzenesulfonyl chloride in 10 ml CH2Cl2 and 32 mg (0.26 mmol) DMAP were added and stirring was continued for 3 h. The mixture was partitioned between CH2Cl2 and a saturated aqueous solution of NaHCO3. The organic phase was washed with water, 1M KHSO4 and brine, dried over Na2SO4 and evaporated. Column chromatography with EtOAc/hexane 1:1 gave 1.06 g (84%) trans-5-{4-[Methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyl}-pentanoic acid diethylamide as colorless oil, MS: 477 (MH+).

Source