Sodium amide → 3-(5,6,7,8-Tetrahydroquinol-8-yl)propylamine

HRID 4509

Reaktionsgleichung

Reaktionsgleichung von HRID 4509
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2-].[Na+].Cl.Cl[CH2:15][CH2:16][CH2:17][NH2:18]>N>[N:1]1[C:10]2[CH:9]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 24533Sodium amideHCID 663355,6,7,8-TetrahydroquinolineHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Produkt 1

HCID 198517793-(5,6,7,8-Tetrahydroquinol-8-yl)propylamineAusbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Versuchsvorschrift

5,6,7,8-Tetrahydroquinoline (20 g) was added quickly to sodamide (17.6 g) in liquid ammonia (250 ml) to give a dark red coloured solution. 3-Chloropropylamine hydrochloride (28.9 g) was added in portions over four hours when loss of colour was permanent after which the reaction was stirred for a further 2 hours and then quenched with ammonium chloride (20 g). The liquid ammonia was allowed to evaporate and the residues were partitioned between chloroform and water. The pH was lowered to 6 and the chloroform layer was discarded. The aqueous layer was basified (pH 12-14), and extracted with chloroform, the chloroform extracts were dried, combined, evaporated and the residue was vacuum distilled to give 3-(5,6,7,8-tetrahydroquinol-8-yl)propylamine (7.58 g), b.p. 92°-94° C. at 0.1 mm Hg.

Aufarbeitung

  1. customto give a dark red coloured solution
  2. customquenched with ammonium chloride (20 g)
  3. customto evaporate
  4. customthe residues were partitioned between chloroform and water
  5. extractionextracted with chloroform
  6. dry with materialthe chloroform extracts were dried
  7. customevaporated
  8. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-218fc6652d2242c19817433db7fef78c
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727076

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