alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide → (R)-2-Amino-5-(3-pyridyl)pentane

HRID 2232130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2232130
OC(C1C=CC=CC=1)C([NH:5][CH:6]([CH3:16])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=O>Cl>[CH3:16][C@@H:6]([NH2:5])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Komponenten

3

Edukt 1

HCID 13999762alphahydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide

Produkt 1

HCID 11062727(R)-2-Amino-5-(3-pyridyl)pentane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel2×

Versuchsvorschrift

A solution of 145 g of [R-(R*,R*)]-alpha-hydroxy-N-[1-methyl-4-(3-pyridinyl)butyl]benzeneacetamide in 900 mL of 6N HCl was treated with 80 mL of conc. HCl and then was heated at reflux for 2 days. After most of the solvent was removed under reduced pressure, the residue was made decidedly basic with 10N NaOH in an argon atmosphere, and extracted with dichloromethane (1×1.2 L; 2×600 mL). The dried (K2CO3) extracts were evaporated and the crude product was distilled to give 78.5 g of (R)-alpha-methyl-3-pyridinebutanamine, (bp 95° C./0.2 mm).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customAfter most of the solvent was removed under reduced pressure
  4. extractionextracted with dichloromethane (1×1.2 L; 2×600 mL)
  5. dry with materialThe dried (K2CO3) extracts
  6. customwere evaporated
  7. distillationthe crude product was distilled

Quellen und Nachweise

ORD-Eintrag
ord-d61917f7814d483f96d3c4392a00e294
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04786646

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