3-Aminopiperidine-2,6-dione hydrochloride → 2-(2,6-Dioxopiperidin-3-yl)-4-(3-ethoxy-4-methoxyphenylamino)-isoindole-1,3-dione

HRID 448339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448339
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:15]([C:16]([OH:18])=O)[C:14]=2[C:22]([OH:24])=O)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].Cl.[NH2:26][CH:27]1[CH2:33][CH2:32][C:31](=[O:34])[NH:30][C:28]1=[O:29]>N1C=CC=CC=1>[O:29]=[C:28]1[CH:27]([N:26]2[C:22](=[O:24])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][C:13]=3[NH:12][C:6]3[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)[C:16]2=[O:18])[CH2:33][CH2:32][C:31](=[O:34])[NH:30]1

Komponenten

4

Edukt 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 583071773-(3-Ethoxy-4-methoxyphenylamino)phthalic acid

Produkt 1

HCID 588273482-(2,6-Dioxopiperidin-3-yl)-4-(3-ethoxy-4-methoxyphenylamino)-isoindole-1,3-dioneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 3-(3-ethoxy-4-methoxyphenylamino)phthalic acid (0.85 g, 2.6 mmol) and rac-α-aminoglutarimide hydrochloride (0.43 g, 2.6 mmol) in pyridine (10 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum. The residue was dissolved in ethyl acetate (150 mL), washed with dilute aqueous HCl (2×100 mL) and water (2×100 mL), and evaporated. The residue was chromatographed in 95:5 methylene chloride-methanol, eluting 0.72 g of the product, in 67% yield: mp 162-164° C.; 1H NMR (CDCl3) δ 1.46 (t, J=7.0 Hz, 3H), 2.11-2.18 (m, 1H), 2.72-2.94 (m, 3H), 3.89 (s, 3H), 4.06 (q, J=7.0 Hz, 3H), 4.96 (dd, J=12.0 Hz, J=5.0 Hz, 1H), 6.76-6.89 (m, 3H), 7.14-7.19 (m, 2H), 7.43 (t, J=7.8 Hz, 1H), 7.86 (s, 1H), 8.43 (s, 1H); 13C NMR (CDCl3) δ 14.7, 22.8, 31.4, 49.0, 56.2, 64.5, 109.9, 110.8, 112.1, 113.1, 116.4, 118.5, 131.7, 132.4, 135.9, 145.2, 147.4, 149.1, 167.5, 168.4, 169.4, 171.1; Anal. calcd for C22H21N3O6: C, 62.41; H, 5.00; N, 9.92. Found: C, 62.16; H, 4.89; N, 9.72.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  6. washwashed with dilute aqueous HCl (2×100 mL) and water (2×100 mL)
  7. customevaporated
  8. customThe residue was chromatographed in 95:5 methylene chloride-methanol
  9. washeluting 0.72 g of the product

Quellen und Nachweise

ORD-Eintrag
ord-40e0dbb58dc5411f8e3c08863ef9aced
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481568B2

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