تفاعل #11728

ord-25061445411d408e8604d629580259c9

معادلة التفاعل

C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)CCl
2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone
O=[N+]([O-])c1cc(Cl)ccc1O
2-nitro-4-chlorophenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[I-].[K+]
potassium iodide
C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-]
title compound
المردود 92.5%
C[C@@H]1CN(Cc2ccc(F)cc2)[C@@H](C)CN1C(=O)COc1ccc(Cl)cc1[N+](=O)[O-]
2-(4-Chloro-2-nitro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone
المردود 92.5%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe reaction mixture was heated
  2. 2
    درجة الحرارةat reflux overnight
  3. 3
    درجة الحرارةThe reaction mixture was then cooled
  4. 4
    استخلاصextracted with ethyl acetate
  5. 5
    تجفيفThe organic layer was dried over magnesium sulfate
  6. 6
    ترشيحfiltered
  7. 7
    تركيزconcentrated
  8. 8
    أخرىto give an orange oil

الإجراء التجريبي

To a solution of 2-chloro-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (1.0 g, 3.35 mmol) in butanone (35 mL) was added 2-nitro-4-chlorophenol (0.64 g, 3.69 mmol), potassium carbonate (0.93 g, 6.7mmol) and potassium iodide (0.56 g, 3.35 mmol). The reaction mixture was heated at reflux overnight. The reaction mixture was then cooled, diluted with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to give an orange oil. Chromatography on silica gel gave the title compound (1.35 g).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07098212B2uspto-grants-2006_08