Sodium Azide → HCID 178420261, compound

HRID 1415152Notes

Reaction equation

HRID 1415152 reaction equation
[C:1]1([C:7]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)([CH2:10][CH2:11][N:12]2[CH2:17][CH:16]3[CH2:18][CH2:19][CH:13]2[CH2:14][CH2:15]3)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[Li+]>CN(C=O)C>[C:1]1([C:7]([C:8]2[NH:28][N:27]=[N:26][N:9]=2)([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH2:10][CH2:11][N:12]2[CH2:17][CH:16]3[CH2:15][CH2:14][CH:13]2[CH2:19][CH2:18]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 203569662-Phenyl-(3-pyridyl)-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile

Product 1

HCID 178420261HCID 178420261, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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-34875127092f4af696f4bf9d18a853f9
Source dataset
uspto-grants-1977_01
Patent number
US04003904

Reaction notes

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