Dimethyl Sulfoxide → 2-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4yl)piperazine-1yl)acetaldehyde

HRID 574291

Reaktionsgleichung

Reaktionsgleichung von HRID 574291
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:39]=[CH:38][C:16]([CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[C:24]3[N:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][OH:37])[CH2:31][CH2:30]2)=[CH:15][CH:14]=1.CCN(CC)CC>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[N:27]=[CH:26][CH:25]=[C:24]3[N:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH:36]=[O:37])[CH2:31][CH2:30]2)=[CH:38][CH:39]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 675044332-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4-yl)piperazine-1-yl)ethanol

Produkt 1

HCID 866646662-(4-(8-((4-Methoxybenzyl)oxy)quinoline-4yl)piperazine-1yl)acetaldehydeAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of oxalyl chloride (1.8 mL, 20.33 mmol) in CH2Cl2 (40 mL) at −78° C. was added DMSO (2.8 mL, 40.66 mmol). The reaction mixture was stirred for 10 minutes followed by addition of compound 26 (4.0 g, 10.16 mmol, solution in 10 mL of CH2Cl2). The reaction mixture was stirred at the same temperature for 12 minutes. Then Et3N (8.4 mL, 60.98 mmol) was added and stirring was continued for another 1 hour and 20 minutes allowing the reaction mixture to come to room temperature. The reaction mixture was quenched by addition of water and extracted with CH2Cl2 (3×75 mL). The combined organic layer was washed with water and brine and finally purified by silica gel column chromatography (EtOAc/MeOH, 9.5:0.5) to yield 3.06 g (77%) of compound 27 as thick oil. 1H NMR (400 MHz, CDCl3) δ ppm 2.45-2.90 (m, 4H), 3.02-3.40 (m, 4H), 3.34 (s, 2H), 3.69 (s, 3H), 5.25 (s, 2H), 6.64-7.04 (m, 4H), 7.16-7.56 (m, 4H), 8.60-8.76 (m, 1H), 9.68 (s, 1H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at the same temperature for 12 minutes
  2. stirringstirring
  3. waitwas continued for another 1 hour and 20 minutes
  4. customto come to room temperature
  5. customThe reaction mixture was quenched by addition of water
  6. extractionextracted with CH2Cl2 (3×75 mL)
  7. washThe combined organic layer was washed with water and brine
  8. customfinally purified by silica gel column chromatography (EtOAc/MeOH, 9.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-3258d595d1984bf2830116c301c687c4
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034877B2

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