Sulfuric Acid → Methyl 4-phenylpiperidine-4-carboxylate

HRID 324321

Reaktionsgleichung

Reaktionsgleichung von HRID 324321
OS(O)(=O)=O.[CH3:6]C1C=CC(S(O)(=O)=O)=CC=1.[C:17]1([C:23]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[CH3:6][O:30][C:29]([C:23]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1)=[O:31]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 27236574-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)

Produkt 1

HCID 545827Methyl 4-phenylpiperidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of H2SO4 (16 mL) in MeOH (400 mL), 4-phenyl-4-piperidinecarboxylic acid 4-methyl benzenesulfonate (37.7 g, 0.1 mole) was added and the mixture was stirred and refluxed for 8 hours. Excess methanol was evaporated at reduced pressure and the residue was poured into a mixture of ice and 6 N NaOH. The pH was adjusted to 10-11 by adding more 6 N NaOH and extracted with CH2Cl2 (3×150 mL). The combined CH2Cl2 extracts were dried (MgSO4) and the solvent evaporated to leave the desired product as a viscous oil. The product (20.2 g, 92%) was used without further purification.

Aufarbeitung

  1. temperaturerefluxed for 8 hours
  2. customExcess methanol was evaporated at reduced pressure
  3. additionthe residue was poured into a mixture of ice and 6 N NaOH
  4. additionby adding more 6 N NaOH
  5. extractionextracted with CH2Cl2 (3×150 mL)
  6. dry with materialThe combined CH2Cl2 extracts were dried (MgSO4)
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b55eaf45509740169295d7897492606a
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218390B1

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