(E)-1-(5-(3,4-dichlorophenyl)furan-2-yl)prop-1-en-2-amine → 1-(5-(3,4-Dichlorophenyl)furan-2-yl)propan-2-amine hydrochloride

HRID 872452

Reaktionsgleichung

Reaktionsgleichung von HRID 872452
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12](/[CH:14]=[C:15](/[NH2:17])\[CH3:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]>CO.CCOC(C)=O.Cl.[Pd]>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][C:12]([CH2:14][CH:15]([NH2:17])[CH3:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

6

Edukt 1

HCID 70655963(E)-1-(5-(3,4-dichlorophenyl)furan-2-yl)prop-1-en-2-amine

Produkt 1

HCID 671701761-(5-(3,4-Dichlorophenyl)furan-2-yl)propan-2-amine hydrochlorideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (E)-1-(5-(3,4-dichlorophenyl)furan-2-yl)prop-1-en-2-amine (2.72 g, 9.12 mmol) in MeOH (135 ml), EtOAc (100 ml) and 6.5% HCl (g) in MeOH (32 ml) was added 10% Pd/C (1.09 g). The mixture was hydrogenated under pressure (3.3 bar, Parr hydrogenating apparatus) for 7 h. The reaction mixture was filtered through Celite, evaporated and purified by chromatography (CombiFlash, silica column, eluent: 5-20% MeOH/DCM) to yield 0.811 g (29%) of the title compound as an HCl salt. 1H-NMR (400 MHz; d6-DMSO): δ 1.21 (d, 3H), 2.90 (dd, 1H), 3.04 (dd, 1H), 3.55 (q, 1H), 6.44 (d, 1H), 7.09 (d, 1H), 7.68 (m, 2H), 7.93 (m, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. customevaporated
  3. custompurified by chromatography (CombiFlash, silica column, eluent: 5-20% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-b5c0dd3e2ef243e3bd9b5b3c95853dc9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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