Chloroacetyl chloride → 2-chloro-N-[2-(2,6-dioxo-3-piperidyl)-1-oxo-isoindolin-4-yl]acetamide

HRID 906732

Reaktionsgleichung

Reaktionsgleichung von HRID 906732
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:19])[C:6]2=[O:11].[Cl:20][CH2:21][C:22](Cl)=[O:23]>C1COCC1.ClCC(Cl)=O>[O:19]=[C:13]1[CH:12]([N:5]2[CH2:4][C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[NH:1][C:22](=[O:23])[CH2:21][Cl:20])[C:6]2=[O:11])[CH2:17][CH2:16][C:15](=[O:18])[NH:14]1

Komponenten

5

Edukt 2

HCID 6577Chloroacetyl chlorideHCID 216326Lenalidomide

Produkt 1

HCID 98808592-chloro-N-[2-(2,6-dioxo-3-piperidyl)-1-oxo-isoindolin-4-yl]acetamideAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6577Chloroacetyl chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred suspension of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (3.89 g, 15.0 mmol) in THF (50 ml) was added chloroacetyl chloride (1.86 g, 16.5 mmol). The mixture was heated to reflux for 45 minutes. To the reaction mixture was added additional chloroacetyl chloride (0.15 g, 0.13 mmol). The reaction mixture was heated at reflux for an additional 30 minutes. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and filtered to give 4.64 g (92%) of product as an off-white solid: 1H NMR (DMSO-d6) δ 11.04 (s, 1H), 10.22 (s, 1H), 7.82 (dd, J=1.6 and 7.2 Hz, 1H), 7.59-7.50 (m, 2H), 5.16 (dd, J=5.1 and 13.2 Hz, 1H), 4.46-4.30 (m, 4H), 3.00-2.85 (m, 1H), 2.65-2.58 (m, 1H), 2.44-2.28 (m, 1H), 2.06-2.01 (m, 1H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 45 minutes
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for an additional 30 minutes
  5. customThe solvent was evaporated in vacuo
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-2f31041a412e47b9932d8caa83b39814
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012997B2

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