Piperazine → HCID 59699580, Verbindung

HRID 901230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901230
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 59699571HCID 59699571, Verbindung

Produkt 1

HCID 59699580HCID 59699580, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-benzyl-4-chloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (4) (1.2 g, 3.5 mmol) in dichloromethane was added slowly to a stirred solution of piperazine (0.9 g, 10.5 mmol) in dichloromethane at room temperature. The solution was stirred overnight at room temperature. The solvent was evaporated and the residue was suspended in water, sonicated briefly, and extracted with dichloromethane. The combined organic phase was subsequently washed by water and brine, dried over Na2SO4, and evaporated to yield 1.12 g (82%) of 1-benzyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (5) as yellow solids. MP: 120° C.; 1H-NMR (DMSO-d6): δ 1.30 (t, J=6.9 Hz, 3H), 2.28 (m, 4H), 3.03 (m, 4H), 4.28 (q, J=6.9 Hz, 2H), 5.55 (s, 2H), 7.16-7.28 (m, 5H), 7.36 (m, 1H), 8.25 (dd, J=1.5, 7.5 Hz, 1H), 8.63 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 393 (M+1), 415 (M+23).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customsonicated briefly
  3. extractionextracted with dichloromethane
  4. washThe combined organic phase was subsequently washed by water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-09c42ebc155c417f845f664aece50f6d
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361760B2

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