Hydrochloric Acid → (3,3,3-Trifluoropropyl)hydrazine dihydrochloride

HRID 1473910Notes

Reaction equation

HRID 1473910 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][CH2:4][NH:5][NH:6]C(OCC1C=CC=CC=1)=O.[ClH:19]>CCO.[Pd]>[ClH:19].[ClH:19].[F:1][C:2]([F:18])([F:17])[CH2:3][CH2:4][NH:5][NH2:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86690727Benzyl 2-(3,3,3-trifluoropropyl)hydrazinecarboxylate

Product 1

HCID 86690726(3,3,3-Trifluoropropyl)hydrazine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To benzyl 2-(3,3,3-trifluoropropyl)hydrazinecarboxylate (1.7 g, 6.49 mmol, 1 eq.) in a mixture of EtOH (30 mL) were added Pd/C (1.0 g) and HCl (12 N, 2.0 mL). The mixture was charged with H2 (60 psi), stirred at rt for 1 h, filtered, and concentrated to give (3,3,3-trifluoropropyl)hydrazine dihydrochloride (1.07 g) as a yellow solid. LRMS (M+H) m/z 129.1.

Workup

  1. additionThe mixture was charged with H2 (60 psi)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-92ef215089544d52b848f68c904cc293
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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