Hydrochloric Acid → N-Formyl-4-(3-aminopropyl)-piperidine hydrochloride

HRID 128211Notes

Reaction equation

HRID 128211 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][N:12]=[N+]=[N-])[CH2:5][CH2:4]1)=[O:2].[H][H].[ClH:17]>[Pd].O.C(OCC)(=O)C>[ClH:17].[CH:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][NH2:12])[CH2:5][CH2:4]1)=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 13503223N-formyl-4-(3-azidopropyl)-piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 23468621N-Formyl-4-(3-aminopropyl)-piperidine hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 10% palladium-on-carbon catalyst (3 g) in water (100 ml), a solution of N-formyl-4-(3-azidopropyl)-piperidine (19.6 g) in ethyl acetate (100 ml) was added. Hydrogen was passed through the mixture, and the pH was maintained at 3.0 by simultaneous addition of 1 N hydrochloric acid. When the consumption of acid ceased, the catalyst was filtered off, and the two layers separated. The aqueous phase was extracted twice with 25 ml portions of ethyl acetate, and thereafter evaporated to dryness in vacuo. The residue was dissolved in propanol-2, filtered, and the filtrate taken to dryness. The residue was treated with acetonitrile, and the crystals were filtered off and washed with acetonitrile followed by ether to give the title compound with m.p. 141°-143° C.

Workup

  1. customWhen the consumption of acid
  2. filtrationthe catalyst was filtered off
  3. customthe two layers separated
  4. extractionThe aqueous phase was extracted twice with 25 ml portions of ethyl acetate
  5. customevaporated to dryness in vacuo
  6. dissolutionThe residue was dissolved in propanol-2
  7. filtrationfiltered
  8. additionThe residue was treated with acetonitrile
  9. filtrationthe crystals were filtered off
  10. washwashed with acetonitrile

Sources & evidence

ORD record
ord-ab5effb060ec42e7b45473d17195b6e8
Source dataset
uspto-grants-1981_03
Patent number
US04259333

Reaction notes

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