تفاعل #332883

ord-93d41685d4594b559bf4b545dc029326

معادلة التفاعل

O=C(OCc1ccccc1)N1CCNCC1
benzyl 1-piperazinecarboxylate
CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
O=C(Cl)OC(Cl)(Cl)Cl
Trichloromethyl chloroformate
O=C(Cl)N1CCN(C(=O)OCc2ccccc2)CC1
benzyl 4-(chlorocarbonyl)piperazine-1-carboxylate

ظروف التفاعل

درجة الحرارة
0°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىwere removed by filtration over decalite
  2. 2
    تركيزthe filtrate was concentrated in vacuo

الإجراء التجريبي

Trichloromethyl chloroformate (5.45 mmol, 0.657 ml) in tetrahydrofuran (20 ml) was cooled to 0° C. and a solution of benzyl 1-piperazinecarboxylate (4.54 mmol, 0.876 ml) and N,N-diisopropylethylamine (9.99 mmol, 1.651 ml) in tetrahydrofuran (20 ml) was added dropwise. After stirring for one hour at 0° C. the solids were removed by filtration over decalite and the filtrate was concentrated in vacuo to give crude benzyl 4-(chlorocarbonyl)piperazine-1-carboxylate. The latter compound was added to 2-aminomethyl-3-chloropyrazine hydrochloride (content 69%; 3.49 mmol, 0.91 g) in dichloromethane (15 ml) and triethylamine (10.46 mmol, 1.458 ml) and the reaction mixture was stirred over night at room temperature. Then the reaction mixture was filtered over decalite (washed with dichloromethane). The filtrate was concentrated and the crude product was purified using column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give benzyl 4-((3-chloropyrazin-2-yl)methylcarbamoyl)piperazine-1-carboxylate (1.15 g).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08658794B2uspto-grants-2014_02