Pyridine → HCID 19029125, compound

HRID 2256034Notes

Reaction equation

HRID 2256034 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19](OCC)([CH3:22])[NH:20][N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[O:18][C:19]([CH3:22])=[N:20][N:21]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 19029164Phenylmethyl 4-(5-ethoxy-4,5-dihydro-5-methyl-1,3,4-oxadiazol-2-yl)-1-piperidinecarboxylate

Product 1

HCID 19029125HCID 19029125, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(5-ethoxy-5-methyl-1,3,4-oxadiazolin-2-yl)piperidine (200 mg) in toluene (5 mL) containing pyridine (0.25 mL) was heated under reflux for 20 hours. The mixture was cooled to room temperature, and the solvent was evaporated. The residue was purified by chromatography, eluting with chloroform:methanol:ammoniumhydroxide (98:2:1), to give the 1,3,4-oxadiazole derivative (0.143 g) as a clear oil; NMR (CDCl3): 7.35 (m, 5), 5.13 (s, 2), 4.16 (broad d, 2, J=12.8), 3.05 (m, 1), 2.50 (s, 3), 2.04 (m, 2), 1.83 (m, 2).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customthe solvent was evaporated
  4. customThe residue was purified by chromatography
  5. washeluting with chloroform:methanol:ammoniumhydroxide (98:2:1)

Sources & evidence

ORD record
ord-fe40d9c154354efb89fb98d1604bdf02
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

Loading…