Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate

HRID 2091757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091757
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].C(N(CC)CC)C.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:28]>ClCCl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][N:13]([C:27]([O:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:28])[CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]2)=[CH:7][CH:8]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58002552Methyl 5-(4-ethylphenyl)piperidine-3-carboxylate

Produkt 1

HCID 580023823-Methyl 1-(4-nitrophenyl) 5-(4-ethylphenyl)piperidine-1,3-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3.0 g (12.1 mmol) of the compound from Example 5A were initially charged in 30 ml of dichloromethane, cooled to 0° C. and admixed with 3.4 ml (2.4 g, 12.1 mmol) of triethylamine and 2.4 g (12.1 mmol) of 4-nitrophenyl chloroformate. The reaction mixture was allowed to warm up slowly to RT and stirred at RT for 16 h. The mixture was washed several times with water, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent dichloromethane→dichloromethane/methanol 100:2). Yield: 4.7 g (83% of theory, purity 89%)

Aufarbeitung

  1. temperatureto warm up slowly to RT
  2. washThe mixture was washed several times with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent dichloromethane→dichloromethane/methanol 100:2)

Quellen und Nachweise

ORD-Eintrag
ord-91d4e7fb9cae4bcbb66c4e1c429cc5a6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440657B2

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