3-Aminopiperidine-2,6-dione hydrochloride → 2-(2,6-Dioxo-3-piperidyl)-4-(pentylamino)isoindoline-1,3-dione

HRID 9997

Reaktionsgleichung

Reaktionsgleichung von HRID 9997
[CH2:1]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:9]([C:10]([OH:12])=O)[C:8]=1[C:16]([OH:18])=O)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[NH2:20][CH:21]1[CH2:26][CH2:25][C:24](=[O:27])[NH:23][C:22]1=[O:28]>C(O)(=O)C>[O:28]=[C:22]1[CH:21]([N:20]2[C:16](=[O:18])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:10]2=[O:12])[CH2:26][CH2:25][C:24](=[O:27])[NH:23]1

Komponenten

4

Edukt 2

HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 219885603-Pentylamino-phthalic acid

Produkt 1

HCID 99026612-(2,6-Dioxo-3-piperidyl)-4-(pentylamino)isoindoline-1,3-dioneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-pentylamino-phthalic acid (2.51 g, 10 mmol) in acetic acid (50 ml) was added 3-amino-piperidine-2,6-dione hydrochloride (1.81 g, 11 mmol). The reaction mixture was heated to reflux overnight. The solvent was evaporated in vacuo and the residue dissolved in ethyl acetate (100 ml). The ethyl acetate mixture was washed with water (2×100 ml), saturated aqueous sodium bicarbonate (2×100 ml), brine (1×100 ml), and dried (MgSO4). The solvent was evaporated in vacuo and the solid residue was purified by chromatography (25% ethyl acetate/hexane) to give 1.82 g (53%) of product as a yellow solid: mp 141–143° C.; 1H NMR (DMSO-d6) d 11.09 (s, 1H), 7.58 (t, J=8.3 Hz, 1H), 7.08 (d, J=8.6 Hz, 1H), 7.02 (d, J=7.0 Hz, 1H), 6.519 (t, J=5.7 Hz, 1H), 5.06 (dd, J=5.3 and 12.4 Hz, 1H), 3.32–3.25 (m, 2H), 2.97–2.82 (m, 1H), 2.62–2.46 (m, 2H), 2.06–2.01 (m, 1H), 1.61–1.55 (m, 2H), 1.35–1.32 (m, 4H), 0.88 (t, J=6.7 Hz, 3H); 13C NMR (DMSO-d6) d 172.72, 170.01, 168.92, 167.25, 146.39, 136.21, 132.14, 117.08, 110.31, 108.99, 48.52, 41.77, 30.94, 28.46, 28.33, 22.12, 21.82, 13.85; Anal. Calcd. For C18H21N3O4: C, 62.96; H, 6.16; N, 12.24. Found: C, 62.92; H, 6.17; N, 12.15.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate (100 ml)
  5. washThe ethyl acetate mixture was washed with water (2×100 ml), saturated aqueous sodium bicarbonate (2×100 ml), brine (1×100 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated in vacuo
  8. customthe solid residue was purified by chromatography (25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7a35a5908175421aac37278eea689741
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091353B2

Verknüpfte Notizen

Wird geladen…