Hydrazine hydrate (1:1) → 5-Methyl-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[4,3-c]pyridine

HRID 1024363Notes

Reaction equation

HRID 1024363 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]=[C:4]([CH:8]=O)[CH2:3]1.O.[NH2:11][NH2:12]>CCCCO>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]2[NH:11][N:12]=[CH:8][CH:4]2[CH2:3]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 154280611-Methyl-3,4-dehydropiperidine-3-carboxaldehyde

Product 1

HCID 593393775-Methyl-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3.2 g 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carbaldehyde was dissolved in 10 mL n-BuOH. Added were 2 equiv. of hydrazine hydrate, the mixture was refluxed for 24 hours and subsequently concentrated in vacuo. The residue was taken up in DCM and extracted with 2M NaOH, and the organic phase was dried over Na2SO4, filtrated and concentrated in vacuo to yield 1.78 g of a brown oil which was used without further purification in the subsequent step.

Workup

  1. additionAdded
  2. temperaturethe mixture was refluxed for 24 hours
  3. concentrationsubsequently concentrated in vacuo
  4. extractionextracted with 2M NaOH
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbe888ed19cf41d8a1222e410537bb9e
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Reaction notes

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