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Dicyclohexylcarbodiimide → 3-(4-(2-(4-Ethoxy-4-oxobutoxy)phenyl)piperazin-1-yl)propyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 887070
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 887070
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[NH:3]1.O[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=2[O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:21][CH2:20]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C1COCC1>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14][CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=4[O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:23][CH2:24]3)=[O:13])=[CH:7][CH:8]=2)[NH:3]1
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Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 132430012-Oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acidHCID 57420184Ethyl 4-(2-(4-(3-hydroxypropyl)piperazin-1-yl)phenoxy)butanoate

Produkt 1

HCID 574201853-(4-(2-(4-Ethoxy-4-oxobutoxy)phenyl)piperazin-1-yl)propyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylic acid 22 (0.21 g, 0.001 mol), ethyl 4-(2-(4-(3-hydroxypropyl)piperazin-1-yl)phenoxy)butanoate 27 (0.38 g, 0.001 mol), dicyclohexylcarbodiimide (0.21 g, 0.001 mol), 4-(dimethylamino)pyridine (0.12 g, 0.001 mol) in 20 mL THF was stirred at room temperature for 12 hours. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated; the residue was diluted with DCM (25 mL). The filtrate was washed with saturated aqueous NaHCO3 solution (25 mL×2) and water (25 mL×2), dried over sodium sulfate (Na2SO4) and evaporated. The residue was purified by silica gel column chromatography using 0-100% gradient of hexane and ethyl acetate to give the pure 3-(4-(2-(4-ethoxy-4-oxobutoxy)phenyl)piperazin-1-yl)propyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate 28. Colorless oil, 0.075 g (13%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.2 Hz, 3H); 1.99 (quintet, J=7.2 Hz, 2H); 2.13 (quintet, J=7.2 Hz, 2H); 2.50-2.65 (m, 8H); 2.99 (t, J=7.6 Hz, 4H); 3.08 (broad s, 4H); 4.01 (t, J=6.4 Hz, 2H); 4.12 (q, J=7.2 Hz, 2H); 4.38 (t, J=6.4 Hz, 2H); 6.81-6.89 (m, 4H); 7.20 (d, J=8.0 Hz, 1H); 7.50 (d, J=1.6 Hz, 1H); 7.64 (dd, J=1.6, 8.0 Hz, 1H, 9.00 (broad s, 1H). MS (ESI): m/z=524.50 (M+H+).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with DCM (25 mL)
  3. washThe filtrate was washed with saturated aqueous NaHCO3 solution (25 mL×2) and water (25 mL×2)
  4. dry with materialdried over sodium sulfate (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-084218354279485fa59b293b77984a51
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247420B2

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