Acetic Anhydride → 5-[1-Phenyl-1-(3-pyridyl)-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-2-methyl-1,3,4-oxadiazole

HRID 1415153Notes

Reaction equation

HRID 1415153 reaction equation
[C:1]1([C:7]([C:24]2NN=[N:26][N:25]=2)([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH2:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:1]1([C:7]([C:24]2[O:31][C:29]([CH3:30])=[N:26][N:25]=2)([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH:14]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH2:13]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178420261HCID 178420261, compound

Product 1

HCID 123006665-[1-Phenyl-1-(3-pyridyl)-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-2-methyl-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

α-Phenyl-3-pyridylacetonitrile (U.S. Pat. No. 3,225,054) is reacted with 2-(2-chloroethyl)-2-azabicyclo[2.2.2]octane in toluene to provide 2-phenyl-2-(3-pyridyl)-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile. This nitrile is reacted with sodium azide in DMF containing lithium chloride to provide 5-[1-phenyl-1-(3-pyridyl)-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1H-tetrazole. Reaction this tetrazole with acetic anhydride in pyridine provides 5-[1-phenyl-1-(3-pyridyl)-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-2-methyl-1,3,4-oxadiazole, the oxalate salt melts at 171°-172° C.

Sources & evidence

ORD record
ord-6b90fb5fbb6a473db25ae16ed44b574b
Source dataset
uspto-grants-1977_01
Patent number
US04003904

Reaction notes

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