Water → N-{1-(Morpholin-4-ylcarbonyl)-5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

HRID 876323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 876323
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[N:26]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(N(CC)CC)C.O>ClCCl>[N:26]1([C:32]([N:13]2[CH2:14][CH:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:24])([F:1])[F:25])[CH:4]=3)[CH2:10][CH:11]([NH:15][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:23])[CH2:12]2)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 66701267N-{5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide

Produkt 1

HCID 66701304N-{1-(Morpholin-4-ylcarbonyl)-5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

At 0° C., 165 mg (0.47 mmol) of N-{5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide were initially charged in 17 ml of dichloromethane, and 71 mg (0.47 mmol) of morpholine-4-carbonyl chloride and 132 μl (0.95 mmol) of triethylamine were added. The mixture was slowly warmed to RT overnight. Water was added, and the reaction mixture was extracted. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 202 mg (92% of theory)

Aufarbeitung

  1. extractionthe reaction mixture was extracted
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Quellen und Nachweise

ORD-Eintrag
ord-43d2da846e0d4d52a773aaff5977ca4c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987248B2

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