Triethylamine → 1-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-piperidinone

HRID 1062426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062426
C(N(CC)CC)C.FC(F)(F)C(O)=O.[NH:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:30]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=2)[CH:31]=[C:32]([C:34](Cl)=[O:35])[N:33]=1>C(Cl)Cl>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[N:30]([C:37]2[CH:38]=[CH:39][C:40]([Cl:43])=[CH:41][CH:42]=2)[CH:31]=[C:32]([C:34]([N:15]2[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)=[O:35])[N:33]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 222853742-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chlorideHCID 222856014-Piperidinone trifluoroacetate

Produkt 1

HCID 222854801-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]carbonyl}-4-piperidinoneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Triethylamine (1.46 mL, 10.45 mmol) was added to a suspension of 4-piperidinone trifluoroacetate (0.76 g, 3.58 mmol) in CH2Cl2 (10 mL) and a solution of 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carbonyl chloride in CH2Cl2 (5 mL) was added. The mixture was stirred at rt under argon for 17 h, diluted with CH2Cl2 (50 mL), washed with water (2×50 mL), dried over MgSO4, and concentrated to give 1-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol4-yl]carbonyl}-4-piperidinone as a yellow solid (0.96 g, 77%). MS (Electrospray) 414 (MH+), 1H NMR (300 MHz, CD2Cl2) δ 7.80 (s, 1H), 7.37-7.20 (m, 6H), 7.06-7.00 (m, 6H), 4.47 (br, 2H), 3.92 (br, 2H), 2.46 (t, 4H).

Aufarbeitung

  1. washwashed with water (2×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-db3bb241873844358236471b1dd27a86
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960601B2

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