HCID 12300651, compound → HCID 12300653, compound

HRID 1415150Notes

Reaction equation

HRID 1415150 reaction equation
Cl.[C:2]1([C:8]([C:25]2[O:29][C:28]([C:30]([O:32]CC)=[O:31])=[N:27][N:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9][CH2:10][N:11]2[CH2:16][CH:15]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH2:14]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[K+]>[C:2]1([C:8]([C:25]2[O:29][C:28]([C:30]([OH:32])=[O:31])=[N:27][N:26]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:9][CH2:10][N:11]2[CH2:16][CH:15]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH2:14]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 12300651HCID 12300651, compound

Product 1

HCID 12300653HCID 12300653, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Thus 2,2-diphenyl-4-(2-azabicyclo[2.2.2]oct-2-yl)butyronitrile described in U.S. Pat. No. 3,318,869 is reacted with sodium azide in DMF to provide 5-[1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1H-tetrazole. This tetrazole is reacted with ethyl chloroglyoxylate in pyridine at -6° C to provide ethyl [1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1,3,4-oxadiazole-2-carboxylate hydrochloride. This ester is hydrolysed in aqueous potassium hydroxide to provide 5-[1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1,3,4-oxadiazole-2-carboxylic acid. Heating this acid for 15 minutes in an oil bath at 130°-140° provides 5-[1,1-diphenyl-3-(2-azabicyclo[2.2.2]oct-2-yl)propyl]-1,3,4-oxadiazole. The hydrochloride salt melts at 233°-234.5° C.

Sources & evidence

ORD record
ord-75afe263af00494392bb21dc61ed6fee
Source dataset
uspto-grants-1977_01
Patent number
US04003904

Reaction notes

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