4-Pyridinecarboxylic acid, 1-oxide → 4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)-piperidine N1-oxide

HRID 275278

Reaktionsgleichung

Reaktionsgleichung von HRID 275278
Cl.CN(C)CCCN=C=NCC.[NH:13]1[CH2:18][CH2:17][C:16](=[C:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][CH2:22][N:21]3[CH:30]=[CH:31][N:32]=[C:20]23)[CH2:15][CH2:14]1.[N+:33]1([O-])[CH:38]=[CH:37][C:36]([C:39](O)=[O:40])=[CH:35][CH:34]=1.O.[OH:44]N1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>ClCCl.O>[N:32]1[CH:31]=[CH:30][N:21]2[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:19](=[C:16]3[CH2:15][CH2:14][N+:13]([O-:44])([C:39]([C:36]4[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=4)=[O:40])[CH2:18][CH2:17]3)[C:20]=12

Komponenten

8

Edukt 5

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 186124926,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine

Produkt 1

HCID 867484844-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)-piperidine N1-oxideAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.61 g) was added to a solution of 6,11-dihydro-11-(4-piperidylidene)-5H-imidazo[2,1-b][3]benzazepine (C, 0.52 g), pyridine-4-carboxylic acid N-oxide (0.44 g) and 1-hydroxybenzotriazole hydrate (0.43 g)in dichloromethane (20 ml) at 0°-5° C. The reaction mixture was then allowed to stir and to warm to 25° C. overnight. Water and 1 M sodium bicarbonate solution were added, and the aqueous layer was extracted with dichloromethane. Combined organic extracts were washed sequentially with water and brine, and were dried, filtered, and concentrated to give 4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)-piperidine N1 -oxide (B, 0.54 g), m.p. 155°-159° C. from carbon tetrachloride-dichloromethane. ##STR26##

Aufarbeitung

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. washCombined organic extracts were washed sequentially with water and brine
  3. customwere dried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c6dc84e46d104623b15d54e6f9a73627
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393753

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