2-Amino-5-chlorobenzophenone → 4-[1-[(6-Chloro-2-methyl-4-phenyl-3-quinolinyl)carbonyl]-4-piperidinyl]benzamide

HRID 1184026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184026
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.O=[C:18]([CH3:37])[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:36]=[CH:35][C:31]([C:32]([NH2:34])=[O:33])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)=[O:21].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(O)C>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:18]([CH3:37])[C:19]([C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH2:34])=[O:33])=[CH:35][CH:36]=3)[CH2:24][CH2:23]1)=[O:21])=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 128702-Amino-5-chlorobenzophenoneHCID 2733225Ytterbium triflateHCID 86641821HCID 86641821, Verbindung

Produkt 1

HCID 462149014-[1-[(6-Chloro-2-methyl-4-phenyl-3-quinolinyl)carbonyl]-4-piperidinyl]benzamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

To a solution of (2-amino-5-chlorophenyl)(phenyl)methanone (693 mg, 3.0 mmol) in ethanol (10 ml) was added 4-(1-(3-oxobutanoyl)piperidin-4-yl)benzamide (893 mg, 3.1 mmol) followed by ytterbium triflate (186 mg, 0.3 mmol). The mixture was heated at 82° C. for 12 hours. The reaction mixture was cooled to room temperature, and the white powder thus obtained was filtered off, washed with ethanol, ethyl acetate, and finally ether to provide 4-(1-(6-chloro-2-methyl-4-phenylquinoline-3-carbonyl)piperidin-4-yl)benzamide (1.1 g, 76%) as a free flowing white powder. 1H NMR (DMSO-d6, 400 MHz) δ: 1 Rotameric forms complicates spectrum, the major rotamer is described; δ 8.09 (d, 1H, J=8.9 Hz); 7.9 (bs, NH, 1H); 7.8 (m, 3H); 7.7-7.5 (m, 6H); 7.25 (bs, NH, 1H); 6.8 (app d, 2H); 4.5 (d, 1H, J=12.9 Hz); 3.4-3.3 (m, 1H); 3.38 (s, 3H); 3.13 (app t, 1H, J=12.9 Hz); 2.8-2.4 (m, 2H); 2.5 (s, 3H); 0.72 (m, 1H); 0.54 (m, 1H). LC MS (CI) shows M+H 484.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe white powder thus obtained
  3. filtrationwas filtered off
  4. washwashed with ethanol, ethyl acetate, and finally ether

Quellen und Nachweise

ORD-Eintrag
ord-47a5c2eb7d544a3a9601eb6aad8f238c
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664399B2

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