Hydrochloric Acid → Piperidine-1-propylamine

HRID 979027

Reaktionsgleichung

Reaktionsgleichung von HRID 979027
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([CH2:13][CH2:14][C:15]([NH2:17])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>C1COCC1.CO>[N:7]1([CH2:13][CH2:14][CH2:15][NH2:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 5667843-(Piperidin-1-yl)propanamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 19049Piperidine-1-propylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To an ice-cooled suspension of LiAlH4 (10.31 g, 0.27 mole) in THF (100 ml), a solution of 1-piperidine-propanamide, 4-(diphenylmethylene) 29.01 g, 0.091 mole) in THF (100 ml) was added dropwise. After stirring for 0.5 hours, the ice-bath was removed, the reaction mixture refluxed for six hours, quenched (EtOAc and 10% NaOH) and the resulting granular precipitate removed by filtration. The filtrate was concentrated to ca 20 ml, dissolved in CHCl3, washed with H2O, and the solvent removed to give a yellow-green oil. This was dissolved in MeOH, treated with HCl gas and the solvent evaporated. The residue crystallized from CH2Cl2 -Et2O to give 1-piperidinepropaneamine, 4-(diphenylmethylene)dihydrochloride hemihydrate as white solid in quantitative yield; mp 249°-252° C.

Aufarbeitung

  1. customthe ice-bath was removed
  2. temperaturethe reaction mixture refluxed for six hours
  3. customquenched (EtOAc and 10% NaOH)
  4. customthe resulting granular precipitate removed by filtration
  5. concentrationThe filtrate was concentrated to ca 20 ml
  6. dissolutiondissolved in CHCl3
  7. washwashed with H2O
  8. customthe solvent removed
  9. customto give a yellow-green oil
  10. customthe solvent evaporated
  11. customThe residue crystallized from CH2Cl2 -Et2O

Quellen und Nachweise

ORD-Eintrag
ord-53ccc46cc5d045bf875dfa360a02ca33
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04666905

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