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

HRID 32167

Reaktionsgleichung

Reaktionsgleichung von HRID 32167
[CH:1]1([CH2:4][CH:5]=O)[CH2:3][CH2:2]1.[CH3:7][C:8]1([CH3:28])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl.C(OCC)(=O)C>[CH:1]1([CH2:4][CH2:5][N:25]2[CH2:26][CH2:27][N:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH:10]3[CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:8]([CH3:28])([CH3:7])[CH2:9]3)[CH2:23][CH2:24]2)[CH2:3][CH2:2]1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 103078492-CyclopropylacetaldehydeHCID 119922841-[2-(3,3,5,5-Tetramethylcyclohexyl)phenyl]piperazine

Produkt 1

HCID 231418781-(2-Cyclopropylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of cyclopropylacetaldehyde in 1,2-dichloroethane (0.29 M, 5 mL) were added 1-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine (25 mg, 0.0832 mmol) produced in Example (8b), sodium triacetoxyborohydride (22.9 mg, 0.108 mmol) and acetic acid (0.009 mL, 0.158 mmol), followed by stirring for 20 minutes at room temperature. Saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and extraction was performed twice with ethyl acetate. The organic layer was concentrated and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 20.9 mg of 1-(2-cyclopropylethyl)-4-[2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine as a colorless oil.

Aufarbeitung

  1. concentrationThe organic layer was concentrated
  2. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-19b23eba74564111ab79266b31c81bff
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425554B2

Verknüpfte Notizen

Wird geladen…