Piperidine → 2-Nitro-5-(piperidin-1-yl)benzoic acid

HRID 1079351

Reaktionsgleichung

Reaktionsgleichung von HRID 1079351
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CC(N(C)C)=O>[N+:11]([C:5]1[CH:4]=[CH:3][C:2]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([O-:13])=[O:12]

Komponenten

4

Edukt 2

HCID 8082PiperidineHCID 172865-Chloro-2-nitrobenzoic acid

Produkt 1

HCID 144593312-Nitro-5-(piperidin-1-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-chloro-2-nitrobenzoic acid (13.7 g), piperidine (27 ml) and DMA (100 ml) was stirred and heated to 120° C. for 18 hours. The mixture was evaporated. The residue was dissolved in water and the solution was basified to pH10 by the addition of 2N aqueous sodium hydroxide solution. The solution was extracted with ethyl acetate. The aqueous layer was acidified to pH2 by the addition of concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give 2-nitro-5-piperidinobenzoic acid (16.25 g), m.p. 130°-140° C.

Aufarbeitung

  1. customThe mixture was evaporated
  2. dissolutionThe residue was dissolved in water
  3. additionthe solution was basified to pH10 by the addition of 2N aqueous sodium hydroxide solution
  4. extractionThe solution was extracted with ethyl acetate
  5. additionThe aqueous layer was acidified to pH2 by the addition of concentrated hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d93b6e40682649339e2f5f6501b5933a
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580870

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