Ethyl Acetate → 1-Acetyl-4-[4-(piperidin-1-yl)phenylamino]piperidine dihydrochloride

HRID 1079395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1079395
[ClH:1].Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[C:16]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)(=[O:18])[CH3:17].C([BH3-])#N.[Na+].C(OCC)(=O)C>CO.O>[ClH:1].[ClH:1].[C:16]([N:19]1[CH2:24][CH2:23][CH:22]([NH:3][C:4]2[CH:5]=[CH:6][C:7]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:8][CH:9]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 122563N-Acetyl-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 233669404-(Piperidin-1-yl)aniline dihydrochloride

Produkt 1

HCID 233669781-Acetyl-4-[4-(piperidin-1-yl)phenylamino]piperidine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of N-(4-aminophenyl)piperidine dihydrochloride obtained in Example 17 and 1-acetyl-4-piperidone (0.70 g) in methanol (10 ml) was added sodium cyano borohydride (0.63 g), followed by stirring at room temperature for 5 hours. To the mixture was added ethyl acetate ester (20 ml) and water (30 ml). After the organic layer was dried over anhydrous sodium sulfate, to the solution was added 6N solution of hydrogen chloride in dioxane (2 ml) and the solvent was distilled off. The residue was recrystallized from ethanol to obtain colorless crystals, m.p. 187°-193° C.

Aufarbeitung

  1. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, to the solution
  2. additionwas added 6N solution of hydrogen chloride in dioxane (2 ml)
  3. distillationthe solvent was distilled off
  4. customThe residue was recrystallized from ethanol
  5. customto obtain colorless crystals, m.p. 187°-193° C.

Quellen und Nachweise

ORD-Eintrag
ord-b29ba32005c44275b8f3f5cd1278e0fa
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580883

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