Sodium hydride → 4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-one

HRID 559354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559354
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6](/[CH:11]=[CH:12]/[C:13]([N:15]2[CH2:20][CH2:19][NH:18][C:17](=[O:21])[CH:16]2[CH3:22])=[O:14])[CH:7]=[CH:8][C:9]=1[Cl:10].[Cl:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CN(C)C(=O)C.C1(C)C=CC=CC=1>[CH2:9]([Cl:10])[Cl:23].[CH3:13][OH:14].[NH4+:15].[OH-:14].[Cl:3][C:4]1[CH:5]=[C:6](/[CH:11]=[CH:12]/[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:17](=[O:21])[CH:16]2[CH3:22])=[O:14])[CH:7]=[CH:8][C:9]=1[Cl:10]

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 630791914-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-piperazin-2-one2×

Produkt 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 575503894-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-3-methyl-1-(3-piperidin-1-yl-propyl)-piperazin-2-oneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium hydride (55% dispersion in mineral oil, 21 mg, 0.48 mmol) was added at room temperature to a solution of 4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-3-methyl-piperazin-2-one (intermediate 1; 100 mg, 0.32 mmol) in N,N-dimethylacetamide (2 ml), then after 20 min a solution of 1-(3-chloropropyl)-piperidine (prepared from the commercially available hydrochloride salt (127 mg, 0.64 mmol) by basic extraction as described in intermediate 6) in toluene (1 ml) was added. The reaction mixture was stirred for 16 h at 50° C., then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; CH2Cl2/MeOH/NH4OH 95:5:0.25) afforded the title compound (66 mg, 47%). Colorless gum, MS (ISP)=438.4 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c5d983ccb3404383a6a857c9d146e19c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063042B2

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