Diisopropylethylamine → 1-(trans-3-(4-Chlorophenyl)allyl)-perhydroazepin-4-one

HRID 83979

Reaktionsgleichung

Reaktionsgleichung von HRID 83979
Cl.[NH:2]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[Cl:19][C:20]1[CH:29]=[CH:28][C:23]([CH:24]=[CH:25][CH2:26]Cl)=[CH:22][CH:21]=1>C(#N)C>[Cl:19][C:20]1[CH:29]=[CH:28][C:23](/[CH:24]=[CH:25]/[CH2:26][N:2]2[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH2:4][CH2:3]2)=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 22021728Azepan-4-one hydrochlorideHCID 53728250p-Chlorocinnamyl chloride

Produkt 1

HCID 689273051-(trans-3-(4-Chlorophenyl)allyl)-perhydroazepin-4-oneAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Perhydroazepinone hydrochloride (2.5 g, prepared according to Synth. Commun. 1992, 1249-1258) was suspended in acetonitrile (80 ml); diisopropylethylamine (4.4 ml) and 4-chlorocinnamyl chloride (2.7 g) were successively added at room temperature and the resulting reaction mixture was stirred at room temperature for 20 hours. The solvent was removed in vacuo and the residue purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4) to afford 1-(trans-3-(4-chlorophenyl)allyl)-perhydroazepin-4-one (1.84 g) as a foam. MS (ES+) 264/266 (M+H+).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by silica gel chromatography (eluent cyclohexane:ethyl acetate 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-ca98a52b02d141e9a3692979e8c3ee85
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846907B2

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