Ethoxalyl chloride → HCID 70128317, compound

HRID 1701570Notes

Reaction equation

HRID 1701570 reaction equation
[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+].[Cl-].[Li+].N1[CH:13]=[N:12][N:11]=N1.[Cl:14][C:15](=[O:21])[C:16]([O:18]CC)=[O:17]>CN(C)C=O.N1C=CC=CC=1>[ClH:14].[O:21]1[CH:13]=[N:12][N:11]=[C:15]1[C:16]([OH:18])=[O:17]

Participants

8

Reactant 5

HCID 20884Ethoxalyl chlorideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 433294Lithium ChlorideHCID 178418441HCID 178418441, compound

Product 1

HCID 70128317HCID 70128317, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

Thus 2,2-diphenyl-4-(4-phenyl-4-piperidinomethanol) butyronitrile is reacted with sodium azide in dimethylformamide along with ammonium chloride and lithium chloride at reflux to prove 5[1,1-diphenyl-3-(4-phenyl-4-piperidinomethanol)propyl]-1H-tetrazole. This tetrazole is reacted with ethyl chloroglyoxylate in pyridine at -6° C. to provide ethyl-5[1,1-diphenyl-4-ethoxyglyoxylmethylpiperidine)propyl]-1,3,4-oxadiazole-2-carboxylate hydrochloride. This ester is hydrolyzed in aqueous potassium hydroxide to provide 5-[1,1-diphenyl-3-(4-phenyl-4-piperidine methanol) propyl]1,3,4-oxadiazole-2-carboxylic acid. Heating this acid provides 5-[1,1-diphenyl-3-(4-phenyl-4-piperidine methanol)propyl]-1,3,4-oxadiazole.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-ed4b79b0c9a64ecf971dd86d1a20d539
Source dataset
uspto-grants-1980_03
Patent number
US04194045

Reaction notes

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