Isopropanol → 6-(3-Methoxyphenyl)-4-Propylmorpholin-3-one

HRID 600222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600222
[OH-].[K+].C(O)(C)C.Cl[CH2:8][C:9]([N:11]([CH2:15][CH:16]([OH:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)[CH2:12][CH2:13][CH3:14])=[O:10]>O>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH:16]2[CH2:15][N:11]([CH2:12][CH2:13][CH3:14])[C:9](=[O:10])[CH2:8][O:25]2)[CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 574406812-Chloro-N-[2-hydroxy-2-(3-methoxyphenyl)ethyl]-N-propylacetamide

Produkt 1

HCID 150064786-(3-Methoxyphenyl)-4-Propylmorpholin-3-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Potassium hydroxide (4.2 g 0.07 mol), isopropyl alcohol (500 ml) and the amide from example 4 (17.8 g, 0.06 mol were stirred together as an opaque solution with water (15 ml) for 2 hours. The reaction mixture was concentrated in vacuo and the yellow residue dissolved in ethyl acetate (200 ml). This was partitioned with water (200 ml) then brine (200 ml). The organic fraction was dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as a yellow oil (15.8 g, 0.06 mol, 100%). 1H NMR (CDCl3, 400 MHz) δ: 0.96 (t, 3H), 1.62 (m, 2H), 3.36 (m, 2H), 3.51 (q, 2H), 3.81 (s, 3H), 4.30-4.62 (bq, 2H), 4.79 (d, 1H), 6.85 (d, 1H), 6.91 (d, 1H), 6.95 (s, 1H), 7.29 (t, 1H). LRMS: m/z 272. Analysis found C, 66.80; H, 7.78; N, 5.52%. C14H19NO30.1H2O requires C, 66.96; H, 7.71; N, 5.58%.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe yellow residue dissolved in ethyl acetate (200 ml)
  3. customThis was partitioned with water (200 ml)
  4. dry with materialThe organic fraction was dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-386b143dfbdb4a9ea77f348549c58094
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902188B2

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