Sulfuric Acid → 8-Benzyl-2,8-diazaspiro[4.5]decane-1,3-dione

HRID 491471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491471
S(=O)(=O)(O)[OH:2].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16]([CH2:21][C:22]#[N:23])([C:19]#N)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-:24].[Na+]>C(O)(=O)C>[CH2:6]([N:13]1[CH2:14][CH2:15][C:16]2([C:19](=[O:24])[NH:23][C:22](=[O:2])[CH2:21]2)[CH2:17][CH2:18]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 128476541-Benzyl-4-(cyanomethyl)piperidine-4-carbonitrile

Produkt 1

HCID 221109398-Benzyl-2,8-diazaspiro[4.5]decane-1,3-dioneAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Acetic acid (56.8 ml) and sulfuric acid (11.8 ml) are added to 1-benzyl-4-cyanomethyl-piperidine-4-carbonitrile (27.2 g, 0.114 mmol) at ambient temperature. The reaction mixture is stirred at 125 C.° for 1 h, cooled down to the room temperature and added to saturated NaOH aq. to adjust to pH 6.0. The mixture is extracted with dichloromethane. The combined extracts are washed with H2O and brine, dried over sodium sulfate and evaporated down to give 8-benzyl-2,8-diaza-spiro[4.5]decane-1,3-dione (three steps yield: 81.8%).

Aufarbeitung

  1. extractionThe mixture is extracted with dichloromethane
  2. washThe combined extracts are washed with H2O and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-bc0498391352468eb616c3b1656b6b4d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531546B2

Notizen zur Reaktion

Wird geladen…