Hydrochloric Acid → 1-(4-fluorobenzyl)piperidin-4-amine(SALTDATA: 1.98HCl 0.75H2O)

HRID 1598376Notes

Reaction equation

HRID 1598376 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([N:13]3C(=O)C4=CC=CC=C4C3=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.O.NN.Cl>C(O)C>[NH2:13][CH:10]1[CH2:9][CH2:8][N:7]([CH2:6][C:5]2[CH:24]=[CH:25][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 18933299HCID 18933299, compound

Product 1

HCID 151324331-(4-fluorobenzyl)piperidin-4-amine(SALTDATA: 1.98HCl 0.75H2O)Yield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(p-fluorobenzyl)-4-phthalimidopiperidine (3.0 g, 8.9 mmol) in ethanol (30 ml) was added hydrazine monohydrate (0.7 ml) and the mixture was heated under reflux for 3 hours. After allowed to cool, to the reaction mixture was added 5N hydrochloric acid (50 ml) and insolubles were filtered off. Then, the filtrate was washed with chloroform (30 ml×3). The aqueous layer was neutralized with potassium carbonate and then extracted with chloroform (50 ml×4). After drying over anhydrous magnesium sulfate, the solvent was distilled off to give 1.7 g of the title compound. Yield=94%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool, to the reaction mixture
  4. filtrationwere filtered off
  5. washThen, the filtrate was washed with chloroform (30 ml×3)
  6. extractionextracted with chloroform (50 ml×4)
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-48123362fc86410da8f799ec9a7d74ad
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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