Hydrochloric Acid → N-{2-[3-(1-Methylpiperidin-2-yl)propyl]phenyl}-3-phenylprop-2-enamide

HRID 1579365ノート

反応式

HRID 1579365 の反応式
CO[C:3]1[CH:27]=[CH:26][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][N:20]2[CH3:25])=[O:8])=[CH:5][CH:4]=1.Cl.[OH-].[Na+].N[C:32]1C=CC=C[C:33]=1CCCC1CCCCN1C.C(Cl)(=O)C=CC1C=CC=CC=1>O.N1C=CC=CC=1.C1COCC1>[CH3:25][N:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[CH2:18][CH2:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:7](=[O:8])[CH:6]=[CH:5][C:4]1[CH:3]=[CH:27][CH:26]=[CH:33][CH:32]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 660233-Phenylprop-2-enoyl chlorideHCID 205599504-Methoxy-N-{2-[3-(1-methylpiperidin-2-yl)propyl]phenyl}benzamideHCID 53764394HCID 53764394、化合物

生成物 1

HCID 53946135N-{2-[3-(1-Methylpiperidin-2-yl)propyl]phenyl}-3-phenylprop-2-enamide収率 46%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-methoxy-2'-[3-(1-methyl-2-piperidyl)propyl]benzanilide (3.5 g., 0.0095 mole) and concentrated HCl (50 ml.) is heated at reflux for 16 hr., diluted with H2O (100 ml.), basified with 50% NaOH, and extracted with Et2O. The Et2O extracts are combined, washed (H2O and saturated NaCl), dried over MgSO4, and concentrated to give 2.2 g. of 2-(o-aminophenylpropyl)-1-methylpiperidine. The amine is dissolved in pyridine (50 ml.) and a solution of cinnamoyl chloride (1.8 g., 0.011 mole) in THF (10 ml.) added. The reaction mixture is stirred for 3 hr., then concentrated to dryness. The residue is dissolved in water, basified with 50% NaOH, and extracted with EtOAc. The EtOAc extracts are washed (H2O + saturated NaCl), dried over magnesium sulfate, and concentrated to give 3.4 g. of oil which is chromatographed on silica AR CC-7 (Mallinckrodt). Elution first with CHCl3 to remove impurities, then with EtOAc to remove the product and concentration of the EtOAc eluate gave 2.3 g. of solid which crystallized from EtOAc yields 1.6 g (46%) of 2'-[3-(1-methyl-2-piperidyl)propyl]cinnamanilide, m.p. 130-132°C. Further crystallization from ethyl acetate-isopropyl ether provides analytically pure product, m.p. 133.5°-134.5°C.

後処理

  1. temperatureat reflux for 16 hr
  2. extractionextracted with Et2O
  3. washwashed (H2O and saturated NaCl)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give 2.2 g
  7. concentration, then concentrated to dryness
  8. dissolutionThe residue is dissolved in water
  9. extractionextracted with EtOAc
  10. washThe EtOAc extracts are washed (H2O + saturated NaCl)
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated
  13. customto give 3.4 g
  14. customof oil which is chromatographed on silica AR CC-7 (Mallinckrodt)
  15. washElution first with CHCl3
  16. customto remove impurities
  17. customwith EtOAc to remove the product and concentration of the EtOAc eluate
  18. customgave 2.3 g
  19. customof solid which crystallized from EtOAc

出典と根拠

ORDレコード
ord-c1ca748465204c88971a74954cdcd83d
出典データセット
uspto-grants-1976_01
特許番号
US03931195

反応ノート

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