3-(1,3-Dioxan-2-yl)aniline → HCID 178512007, Verbindung

HRID 659125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659125
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].C[Al](C)C.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][C:20]=1[C:31]#[N:32]>C1(C)C=CC=CC=1.CCCCCCC.C(Cl)Cl.CO>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:8]=[C:9]([NH:10][C:31]([C:20]2[CH:21]=[C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:23]=[CH:24][C:19]=2[F:18])=[NH:32])[CH:11]=[CH:12][CH:13]=1

Komponenten

7

Edukt 3

HCID 6016073-(1,3-Dioxan-2-yl)anilineHCID 16682925TrimethylaluminumHCID 46314739HCID 46314739, Verbindung

Produkt 1

HCID 178512007HCID 178512007, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel2×HCID 8900HeptaneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To 3-(1,3-dioxan-2-yl)aniline (55) (336 mg, 1.87 mmol) in toluene (7.5 mL) cooled to 0° C. was added a 2M trimethylaluminum solution in heptane (1.32 mL) dropwise and the resulting mixture was stirred at ambient temperature for 3.5 hours. The nitrile (54) (370 mg, 1.88 mmol) in toluene (7.5 mL) was added and the reaction heated to 70° C. overnight. The reaction was then cooled, poured onto a slurry of silica in DCM/MeOH and the organics flushed through with further DCM/MeOH. The filtrate was concentrated in vacuo and the residue purified by column chromatography using a gradient of EtOAc in heptane (5-100%) to yield the title compound. Yield: 378 mg, 53%; LC-MS tr 1.32 min; HPLC Purity: 71%; MS (ES+) m/z 377 (M+H)

Aufarbeitung

  1. temperaturethe reaction heated to 70° C. overnight
  2. temperatureThe reaction was then cooled
  3. customthe organics flushed through with further DCM/MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6f27497884c9483ebcf2bfaaa9559680
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080567B2

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