Hydrochloric Acid → 4-Carbamoyl-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 917100Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917100
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:23].[Na+].Cl>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14](=[O:23])[NH2:15])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49760270tert-Butyl 4-(4-chlorophenyl)-4-cyanopiperidine-1-carboxylate

Produkt 1

HCID 450739964-Carbamoyl-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid tert-butyl esterAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-chloro-phenyl)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 1.56 mmol) in ethanol (15 ml) was added 2 ml 10 N aqueous sodium hydroxide. The resulting solution was warmed to reflux for 2 hours, cooled to room temperature, poured into 1 N aqueous hydrochloric acid, and extracted into ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. Recovered yellow oil was purified by silica gel chromatography, eluting with dichloromethane-methanol (9.6:0.4) to give the title compound (306 mg, 58%). MS m/z: 339 (M+1)

Aufarbeitung

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux for 2 hours
  3. extractionextracted into ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customRecovered yellow oil
  8. customwas purified by silica gel chromatography
  9. washeluting with dichloromethane-methanol (9.6:0.4)

Quellen und Nachweise

ORD-Eintrag
ord-37f881a59dc4407582feea92f5f7978e
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271176B2

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