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

HRID 574291ノート

反応式

HRID 574291 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3258d595d1984bf2830116c301c687c4
出典データセット
uspto-grants-2015_05
特許番号
US09034877B2

反応ノート

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