Methyl morpholine oxide → HCID 86676738, Verbindung

HRID 709305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 709305
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[C:14]([C:26]([F:29])([F:28])[F:27])[CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:2]([C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[C:14]([C:26]([F:29])([F:28])[F:27])[CH:13]=2)[CH:6]=[CH:7][C:8]=1[CH3:9])=[O:1]

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 67326247HCID 67326247, Verbindung

Produkt 1

HCID 86676738HCID 86676738, VerbindungAusbeute 88.770,797 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of N-(3-(hydroxymethyl)-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide (200 mg, 0.47 mmol) in CH2Cl2 (2 mL) was added freshly dried 4 Å MS and NMO (83 mg, 0.71 mmol). The mixture was stirred for 10 min before TPAP (17 mg, 0.05 mmol) was added, and the resulting reaction mixture was stirred 12 hours at room temperature. The reaction mixture was filtered through celite, concentrated under reduced pressure, and purified by flash column chromatography (3% to 7% MeOH/CH2Cl2) to afford title product (175 g, 88% yield). MS m/z: 420 [M+1].

Aufarbeitung

  1. additionwas added
  2. customthe resulting reaction mixture
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography (3% to 7% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-4b2b8e63b36e47f9ba4938f8d4d80330
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09180127B2

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