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 1791364Notes

Reaction equation

HRID 1791364 reaction equation
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

Participants

3

Reactant 1

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

Product 1

HCID 103549563-(5-Piperidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrileYield 77.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
45 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-66a50e87870749f6a6723fc9a87525a5
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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