Propylamine → 8-chloro-2-(N-n-propylamino)tetralin

HRID 274800

Reaktionsgleichung

Reaktionsgleichung von HRID 274800
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=O)[CH2:8][CH2:7]2.[CH2:13]([NH2:16])[CH2:14][CH3:15].[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH2:13]([NH:16][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

Komponenten

5

Edukt 3

HCID 7852PropylamineHCID 4311764Sodium borohydrideHCID 46232698-Chloro-1,2,3,4-tetrahydronaphthalen-2-one

Produkt 1

HCID 149692298-chloro-2-(N-n-propylamino)tetralin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

8-Chloro-2-tetralone (500 mg, 2.78 mMol) in toluene (25 mL) was reacted with propylamine (1.14 mL, 13.9 mMol) and sodium borohydride (500 rag) as described in Example2 to give after purification by flash chromatography (5% methanol in dichloromethane+tr. NH4OH) the title compound as a dark oil (340 mg, 55%). The hydrochloride was formed, and recrystallization (ethanol/diethyl ether) gave a colorless, crystalline solid (m.p.=213°-215° C.).

Aufarbeitung

  1. customto give
  2. customafter purification by flash chromatography (5% methanol in dichloromethane+tr. NH4OH) the title compound as a dark oil (340 mg, 55%)

Quellen und Nachweise

ORD-Eintrag
ord-9d681bdd390848d68b15aa5fbf35ee22
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389687

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