تفاعل #1435745

ord-7a4df0aa5ce14d80a59cf2829f16ebe3

معادلة التفاعل

CN(C)C1CCNCC1.Cl.Cl
Dimethyl-piperidin-4-yl-amine dihydrochloride
O=[N+]([O-])c1ccc(F)cc1
4-fluoro-nitrobenzene
Cl
HCl
CN(C)C1CCN(c2ccc([N+](=O)[O-])cc2)CC1
desired product
CN(C)C1CCN(c2ccc([N+](=O)[O-])cc2)CC1
Dimethyl-[1-(4-nitro-phenyl)-piperidin-4-yl]-amine

المذيبات

ظروف التفاعل

درجة الحرارة
90°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصextracted with diethyl ether (2×10 mL)
  2. 2
    workup.ADDITIONThe aqueous layer was treated with saturated sodium carbonate to pH=10
  3. 3
    استخلاصextracted with methylene chloride (2×20 mL)
  4. 4
    تجفيفThe organic layer was dried with sodium sulfate
  5. 5
    أخرىthe solvent was removed

الإجراء التجريبي

Dimethyl-piperidin-4-yl-amine dihydrochloride (Aldrich, 2.0 g, 9.95 mmol) and 4-fluoro-nitrobenzene (Aldrich, 2.5 g, 17.7 mmol) were added to methanol (30 mL). The mixture was heated to 90° C. and stirred for 3.5 hours. The mixture was treated with 1 N HCl to pH=1 and then extracted with diethyl ether (2×10 mL). The aqueous layer was treated with saturated sodium carbonate to pH=10 and then extracted with methylene chloride (2×20 mL). The organic layer was dried with sodium sulfate and the solvent was removed to give the desired product. 1.25 g, 50%. MS (m+H)+: 250.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07211576B2uspto-grants-2007_05