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Hydrochloric Acid → N-(piperidin-4-yl)pyridin-3-amine

HRID 28126
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 28126
C1(C[N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:10][CH2:9]2)C=CC=CC=1.CO.Cl.[H][H]>[Pd].O>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10706957N-[1-(phenylmethyl)-4-piperidinyl]-3-pyridinamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22393771N-(piperidin-4-yl)pyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 20 parts of N-[1-(phenylmethyl)-4-piperidinyl]-3-pyridinamine, 160 parts of methanol, 30 parts of water and 12 parts of a concentrated hydrochloric acid solution is hydrogenated at normal pressure and at a temperature between 22°-39° C., in the presence of 7 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, hydrogenation is stopped. The catalyst is filtered off and the filtrate is evaporated. The oily residue is dissolved in water. This solution is rendered alkaline with ammonium hydroxide, saturated with solid potassium carbonate and then extracted with methylbenzene. The extract is dried over potassium carbonate and evaporated. The solid residue is recrystallized from a mixture of 40 parts of benzene and 32 parts of 1,1'-oxybisethane, yielding 3 parts of N-(4-piperidinyl)-3-pyridinamine; mp. 127°-129° C.

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionThe oily residue is dissolved in water
  4. extractionsaturated with solid potassium carbonate and then extracted with methylbenzene
  5. dry with materialThe extract is dried over potassium carbonate
  6. customevaporated
  7. customThe solid residue is recrystallized from a mixture of 40 parts of benzene and 32 parts of 1,1'-oxybisethane

Quellen und Nachweise

ORD-Eintrag
ord-a8c77a8363bd4bd2b48394630ffccb7b
Quelldatensatz
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04225606

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