Formaldehyde → 2-(1-[Indol-3-ylmethyl]piperid-4-yl)-1H-isoindole-1,3-(2H)-dione

HRID 1578110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1578110
C=O.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])[CH2:15][CH2:14]1.[C:30]([O-])(=O)C.[Na+]>C(O)(=O)C.O>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:30][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:20](=[O:29])[C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]3=[O:28])[CH2:15][CH2:14]2)=[CH:4]1

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 798IndoleHCID 517045Sodium AcetateHCID 218825602-(Piperidin-4-yl)isoindoline-1,3-dione hydrochloride

Produkt 1

HCID 205688982-(1-[Indol-3-ylmethyl]piperid-4-yl)-1H-isoindole-1,3-(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Formaldehyde (0.84 cm3, 40% aq. w/v, 11.3 mmol) was added to a stirred and cooled mixture of indole (1.32 g, 11.3 mmol), 2-(piperid-4-yl)-1H-isoindol-1,3-(2H)-dione, hydrochloride (3.0 g, 11.3 mmol), and sodium acetate (0.93 g, 11.3 mmol) in glacial acetic acid (10 cm3). The suspension was stirred at room temperature for 5 hours, then poured into water and a gummy precipitate filtered off. The mother liquors were basified by addition of 0.880 ammonia to precipitate the title compound, which was collected and dried (2.52 g, 62.4%).

Aufarbeitung

  1. temperaturecooled
  2. stirringThe suspension was stirred at room temperature for 5 hours
  3. filtrationa gummy precipitate filtered off
  4. additionThe mother liquors were basified by addition of 0.880 ammonia
  5. customto precipitate the title compound, which
  6. customwas collected
  7. customdried (2.52 g, 62.4%)

Quellen und Nachweise

ORD-Eintrag
ord-1eb450068dfb450db327d477248e24e9
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04291042

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