Water → N-(beta-n-butoxyacryloyl)-N-(1-benzyl-4-piperidinyl)aniline

HRID 483482

Reaktionsgleichung

Reaktionsgleichung von HRID 483482
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:28]([O:32][CH:33]=[CH:34][C:35](Cl)=[O:36])[CH2:29][CH2:30][CH3:31].O>C(OC(C)C)(C)C>[CH2:28]([O:32][CH:33]=[CH:34][C:35]([N:14]([CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:36])[CH2:29][CH2:30][CH3:31]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 70865N-Phenyl-1-(phenylmethyl)-4-piperidinamineHCID 534397723-Butoxyprop-2-enoyl chloride

Produkt 1

HCID 54210636N-(beta-n-butoxyacryloyl)-N-(1-benzyl-4-piperidinyl)anilineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7914Diisopropyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of N-(1-benzyl-4-piperidinyl)aniline (1.8 g), diisopropyl ether (20 ml) and triethylamine (0.87 g) is added dropwise a solution of β-n-butoxyacrylic acid chloride (1.4 g) in diisopropyl ether (5 ml) with stirring and heating at 70° C. After completion of dropwise addition, the mixture is further stirred with heating at the same temperature for 0.5 hour. After cooling, water is added to the reaction mixture and the mixture is subjected to extraction with ethyl acetate. The extract is washed with water and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography to give N-(β-n-butoxyacryloyl)-N-(1-benzyl-4-piperidinyl)-aniline (2.6 g).

Aufarbeitung

  1. additionAfter completion of dropwise addition
  2. stirringthe mixture is further stirred
  3. temperaturewith heating at the same temperature for 0.5 hour
  4. temperatureAfter cooling
  5. extractionthe mixture is subjected to extraction with ethyl acetate
  6. washThe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent is distilled off under reduced pressure
  9. customthe resulting residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-961a585b2cfe4d859a4bab81ab32d461
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225402

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