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

HRID 12502Notes

Reaction equation

HRID 12502 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-67e561b31978414c8fcba4efacbbcbe9
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Reaction notes

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