Indolin-1-amine hydrochloride → 4,5,7,8-Tetrahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indol-10(9H)-one

HRID 358566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358566
Cl.N[N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[O:12]=[C:13]1[CH2:18][C:17](=O)[CH2:16][CH2:15][NH:14]1>C(O)C>[CH:9]1[CH:8]=[CH:7][C:6]2[CH2:5][CH2:4][N:3]3[C:11]=2[C:10]=1[C:18]1[C:13](=[O:12])[NH:14][CH2:15][CH2:16][C:17]=13

Komponenten

4

Edukt 2

HCID 2760931Indolin-1-amine hydrochlorideHCID 108878632,4-Piperidinedione

Produkt 1

HCID 200665384,5,7,8-Tetrahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indol-10(9H)-oneAusbeute 201 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1-amino-indoline hydrochloride (1.0 g) and 2,4-dioxopiperidine (663 mg) in absolute ethanol (40 ml) was stirred under nitrogen for 48 h. The solvent was removed in vacuo and the residue was dissolved in diethylene glycol (30 ml) and heated at 200° for 2 h. The solution was allowed to cool, poured into water (200 ml) and extracted with dichloromethane (3×100 ml). The combined, dried organic extracts were evaporated to give an oil (ca. 2.5 g) which was purified by short path column chromatography on silica gel (Merck 7729) eluting with System A (400:10:1) to give the title compound (330 mg) as a solid, m.p. 265°-267°.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in diethylene glycol (30 ml)
  3. temperatureheated at 200° for 2 h
  4. temperatureto cool
  5. additionpoured into water (200 ml)
  6. extractionextracted with dichloromethane (3×100 ml)
  7. customdried organic extracts were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2940da54f1474d00b50aaa2687c119c8
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997831

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