Sodium Hydroxide → 4-(3-(1-Methylethoxy)phenyl)-1-piperidinecarboxylic acid phenyl ester

HRID 397739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397739
C([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=2)[CH2:5][CH2:4]1)C.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:23]1([O:22][C:20]([N:3]2[CH2:8][CH2:7][CH:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=3)[CH2:5][CH2:4]2)=[O:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 23001057N-Ethyl-4-(3-(1-methylethoxy)phenyl)piperidine

Produkt 1

HCID 537251114-(3-(1-Methylethoxy)phenyl)-1-piperidinecarboxylic acid phenyl esterAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To N-ethyl-4-(3-(1-methylethoxy)phenyl)piperidine (Preparation 45, 2.0 g, 8.10 mmol) in toluene (20 ml) at 85° C. was added phenyl chloroformate (1.0 ml, 9.70 mmol) and the mixture was heated at reflux for 4 h. The solution was cooled to 45° C. and aqueous sodium hydroxide solution (1 ml of 50% aqueous sodium hydroxide solution in 8 ml of water) was added. The reaction mixture was cooled to room temperature and the organic layer was separated and washed with methanol: 1N aqueous hydrochloric acid (1:1, 2×20 ml), methanol: 1N aqueous sodium hydroxide solution (1:1, 25 ml) and water (20 ml). The organic extract was dried (MgSO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica column chromatography eluting with ethyl acetate:hexane (1:5) to give the title compound as an oil (1.7 g, 62%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe organic layer was separated
  5. washwashed with methanol
  6. extractionThe organic extract
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give the crude product
  11. customThis was purified by silica column chromatography
  12. washeluting with ethyl acetate:hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-55fc36ca6aa6455d98b4508a4be3a999
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610711B2

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