Hydrazine hydrate (1:1) → Quinuclidine-3-carbohydrazide

HRID 1073114Notes

Reaction equation

HRID 1073114 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11]C)=O)[CH2:2]2.O.[NH2:14][NH2:15]>O.C(=O)([O-])[O-].[K+].[K+]>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([NH:14][NH2:15])=[O:11])[CH2:2]2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2736953Methyl quinuclidine-3-carboxylate

Product 1

HCID 573413Quinuclidine-3-carbohydrazideYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 11430Potassium CarbonateSolvent

Procedure

(±) Methyl 1-azabicyclo[2.2.2]octane-3-carboxylate* (0.36 g; 2.1 mmoles) and hydrazine hydrate (0.35 ml; 7.0 mmoles) were heated at 120° C. for 2 h. The reaction was diluted with water (10 ml), saturated with potassium carbonate and extracted into chloroform (3×15 ml). Combined organic extracts were dried (Na2SO4) and concentrated to give the title compound as a pale oil (0.36 g; 100%) which was used in the next stage without further purification. *

Workup

  1. extractionextracted into chloroform (3×15 ml)
  2. dry with materialCombined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0f50e22830d14977ab82e6f434ef78a4
Source dataset
uspto-grants-1990_11
Patent number
US04968691

Reaction notes

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