Acetic Acid → 1-Butyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

HRID 32146

Reaktionsgleichung

Reaktionsgleichung von HRID 32146
[CH3:1][C:2]1([CH3:22])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:3]1.[CH:23](=O)[CH2:24][CH2:25][CH3:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:23]([N:19]1[CH2:18][CH2:17][N:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:4]2[CH2:3][C:2]([CH3:22])([CH3:1])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5]2)[CH2:21][CH2:20]1)[CH2:24][CH2:25][CH3:26]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 261ButanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 119922841-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazine

Produkt 1

HCID 112797551-Butyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazineAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (300 mg, 1.00 mmol) prepared in Example (8b) in tetrahydrofuran (20 mL) were added butyraldehyde (107 mg, 1.49 mmol), sodium triacetoxyborohydride (420 mg, 1.99 mmol) and acetic acid (60 mg, 0.99 mmol) in that order, the mixture was stirred at room temperature for 13 hours and 30 minutes. After the reaction completed, saturated aqueous sodium hydrogencarbonate was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the desiccant was filtered and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 270 mg of 1-butyl-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine as a light yellow oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-856a387185174a6180f19db4fe961279
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

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