Hydrochloric Acid → 2-Methyl-5-(2-piperazin-1-ylethoxy)quinoline

HRID 1295568ノート

反応式

HRID 1295568 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[N:3]=1.Cl.C(OCC)C>C(O)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[N:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11394642tert-Butyl 4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazine-1-carboxylate

生成物 1

HCID 112542672-Methyl-5-(2-piperazin-1-ylethoxy)quinoline収率 91%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

tert-Butyl 4-[2-(2-methylquinolin-5-yloxy)ethyl]piperazine-1-carboxylate (1.04 g, 2.8 mmol) was dissolved in ethanol (60 mL) and treated with 1 M hydrochloric acid in diethyl ether (16 mL, 16 mmol) and stirred at 40° C. for 17 h. The reaction mixture was filtered and the white solid was collected and dried in vacuo. The hydrochloride salt precipitate was dissolved in water (25 mL) and potassium carbonate was added until the pH reached 10. The aqueous layer was washed with 5% methanol in dichloromethane (4×100 mL) then 10% methanol in dichloromethane (4×100 mL). The organic layers were combined, dried (Na2SO4) and concentrated in vacuo, affording the title compound as a brown oil (0.69 g, 91%).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customthe white solid was collected
  3. customdried in vacuo
  4. dissolutionThe hydrochloride salt precipitate was dissolved in water (25 mL)
  5. additionpotassium carbonate was added until the pH
  6. washThe aqueous layer was washed with 5% methanol in dichloromethane (4×100 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2f53d0bbd9f543a299506b8d11dd627e
出典データセット
uspto-grants-2007_07
特許番号
US07244726B2

反応ノート

読み込み中…