Réaction #89763

Équation de réaction

methyl(3R,4S)-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate

acetonitrile

triethylamine

diphenyl cyanocarbonimidate

→

methyl(3R,4S)-1-[(Z)-(cyanoimino)(phenoxy)methyl]-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was heated
2. 2
   ConcentrationThe reaction mixture was concentrated in vacuo
3. 3
   AutreThe residue was purified by Combiflash with 40-90% EtOAc/Hex
4. 4
   Autreto give
5. 5
   Autrethe product (60% in yield)

Mode opératoire

To a stirred solution of methyl(3R,4S)-4-[4-(4-cyano-2-methylphenyl)piperazin-1-yl]carbonylpiperidine-3-carboxylate (386.500 mg, 1.04334E-3 mol) in anhydrous acetonitrile (6.000 mL, 0.1149 mol) at rt was added triethylamine (0.2923 mL, 0.002087 mol) and diphenyl cyanocarbonimidate (384.4 mg, 0.001565 mol). The reaction mixture was heated to reflux (oil bath temperature: 85° C.) for 5 hrs. The reaction mixture was concentrated in vacuo. The residue was purified by Combiflash with 40-90% EtOAc/Hex to give the product (60% in yield). MS (ESI): (M+H)+=515.

Source