Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate → 3-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile

HRID 1791364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791364
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[N:15]=1)=O)(C)(C)C>C(O)=O>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=2)[C:25]#[N:26])[N:15]=1

Komponenten

3

Edukt 1

HCID 69619392Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate

Produkt 1

HCID 103549563-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrileAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester (8.1 g) was mixed with 96% formic acid (80 mL) and heated at 45° C. for 1 h. The reaction mixture was concentrated in vacuo. The residue was quenched with saturated sodium bicarbonate and extracted with dichloromethane. The organic layer was dried with sodium sulfate and concentrated again. The residue was triturated with hexanes to give 4.5 g (73.4%) of the title compounds as a white solid. 1H NMR (CDCl3), δ(ppm): 8.41 (s, 1H), 8.33 (d, 1H), 7.78 (dd, 1H), 7.61 (t, 1H), 4.15 (dd, 1H), 3.20 (m, 1H), 2.84 (m, 1H), 2.14 (m, 1H), 1.55–2.00 (m, 5H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was quenched with saturated sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated again
  6. customThe residue was triturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-66a50e87870749f6a6723fc9a87525a5
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074809B2

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