Hydrazine → HCID 131711759, compound

HRID 1395431Notes

Reaction equation

HRID 1395431 reaction equation
[C:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH2:11][CH:12]2[CH2:17][CH:16]3[CH2:18][CH2:19][N:13]2[CH2:14][CH2:15]3)[C:8]([O-:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:26][NH2:27]>CO>[C:1]1([C:7]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([CH2:11][CH:12]2[CH2:17][CH:16]3[CH2:18][CH2:19][N:13]2[CH2:14][CH2:15]3)[C:8]([NH:26][NH2:27])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 131711760HCID 131711760, compound

Product 1

HCID 131711759HCID 131711759, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to this method, 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]octan (IV) is treated with a butyl lithium solution in the presence of N,N,N',N-tetramethylethylenediamine followed by methyl chloroformate to yield 2,2-diphenyl-3-(1-azabicyclo[2.2.2]-oct-2-yl)propionate (V). Then the propionate (V) is treated with a solution of H2NNH2 in CH3OH to yield 2,2-diphenyl-3-(1-azabicyclo[2.2.2]-oct-2-yl)propionic acid hydrazide (VI). The hydrazide (VI) is then mixed with CH3C(OC2H5)3 to provide the product (VII), i.e., 2-[2-(5-methyl-1,3,4-oxadiazol-2-yl)-2,2-diphenylethyl]-1-azabicyclo 2.2.2 octane.

Sources & evidence

ORD record
ord-a00d5d23f43943019f2545eed8f506b9
Source dataset
uspto-grants-1980_05
Patent number
US04203990

Reaction notes

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