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Acetic Acid → (+/-)-1-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}piperazine

HRID 2307103
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2307103
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][C:17](=O)[CH2:16]1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(O)(=O)C>ClC(Cl)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:16]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 4837Piperazine2×HCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)2×HCID 22337753(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone

Produkt 1

HCID 22337793(+/-)-1-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone (80 mg) and piperazine (24 mg) were dissolved in dichloroethane (5 ml) and stirred at ambient temperature for 1 hr under argon. Tetramethylammonium triacetoxyborohydride (79 mg) was added and stirring continued under argon. After 16 hr, additional portions of piperazine (24 mg) and tetramethylammonium triacetoxyborohydride (79 mg) were added and stirring continued. After a further 6 hr, glacial acetic acid was added dropwise until a solution was obtained, and stirring continued at ambient temperature. After a further 16 hr, the reaction mixture was partitioned between sodium hydrogen carbonate (20 ml of a saturated solution) and ethyl acetate. The aqueous layer was extracted with ethyl acetate (3×20 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude residue was purified by flash column chromatography chromatography (SiO2, dichloromethane/methanol, 9:1 v/v) to furnish the title compound as an off white solid (52 mg, 53%) and mixture of diastereoisomers; m/z (ES+) 365 (M+H)+.

Aufarbeitung

  1. stirringstirring
  2. waitAfter 16 hr
  3. stirringstirring
  4. waitAfter a further 6 hr
  5. customwas obtained
  6. stirringstirring
  7. customcontinued at ambient temperature
  8. waitAfter a further 16 hr
  9. customthe reaction mixture was partitioned between sodium hydrogen carbonate (20 ml of a saturated solution) and ethyl acetate
  10. extractionThe aqueous layer was extracted with ethyl acetate (3×20 ml)
  11. dry with materialthe combined organic extracts were dried over magnesium sulfate
  12. customevaporated in vacuo
  13. customThe crude residue was purified by flash column chromatography chromatography (SiO2, dichloromethane/methanol, 9:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-d60cd5cbace34488b43cf98842305d33
Quelldatensatz
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06828460B2

Notizen zur Reaktion

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