Hydrochloric Acid → HCID 67323942, Verbindung

HRID 1257631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257631
C([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])[C:17](=[O:32])[CH2:16]1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[NH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:23]=2[O:30][CH3:31])[C:17](=[O:32])[CH2:16]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 67323870HCID 67323870, Verbindung

Produkt 1

HCID 67323942HCID 67323942, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of racemic 4-(benzhydryl-amino)-1-(2,4-dimethoxy-benzyl)-piperidin-2-one (3.30 g, 7.80 mmol), 10% Pd on carbon (410 mg, 0.39 mmol) and 2M aqueous HCl (4 mL, 8.15 mmol) in ethanol (150 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 23 hours. The reaction mixture was filtered through Celite® which was washed with ethanol, and the filtrate concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel (gradient: 2M NH3 in methanol solution in DCM) to afford 1.53 g (75%) of 4-amino-1-(2,4-dimethoxy-benzyl)-piperidin-2-one as an oil. LCMS (Method I, ESI): RT=1.57 min, m+H=265.3; 1H NMR (400 MHz, CDCl3) δ: 7.15 (d, 1H), 6.46-6.42 (m, 2H), 4.56 (m, 2H), 3.80 (m, 6H), 3.33 (dt, 1H), 3.22 (m, 2H), 2.69 (ddd, 1H), 2.21 (dd, 1H), 1.94 (m, 1H), 1.59 (dtd, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite® which
  2. washwas washed with ethanol
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe resulting residue was purified by column chromatography on silica gel (gradient: 2M NH3 in methanol solution in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-cf4069e8da814df9958a994ea5583236
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461328B2

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