Potassium Carbonate → 2-(1-Piperidyl)ethyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate

HRID 609591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 609591
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:11])=[CH:2]1.ClN1[C:26](=[O:27])[CH2:25][CH2:24]C1=O.BrCCCO.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:27]1[C:2]2=[C:3]([C:10]([O:12][CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:11])[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[N:1]2[CH2:24][CH2:25][CH2:26]1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 31398ChlorosuccinimideHCID 3272300SB 203186

Produkt 1

HCID 195994092-(1-Piperidyl)ethyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylateAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-(1-Piperidyl)ethyl 1H-indole-3-carboxylate was treated initially with N-chlorosuccinimide (1.5 equivalents) for 2 h, then with 3-bromo-1-propanol (3 equivalents) for 21 h, followed by anhydrous potassium carbonate in acetone, using the method described in Example 1b. The crude product was purified using the same chromatography conditions as in Example 1b to afford the title compound (E4) as a pale yellow oil (15%). This was converted to its oxalate salt and crystallised from acetone mp 174-177° C.

Aufarbeitung

  1. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-f43640d91cbd42698fd8eccae4917238
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998409

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