Sodium Iodide → 2-(3-Cyano-3,3-diphenylpropyl)-1-(3,4-methylenedioxyphenethyl)piperidine

HRID 974965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974965
[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)#[N:2].[CH2:24]1[O:35][C:34]2[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]Br)=[CH:27][C:26]=2[O:25]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(OCC)(=O)C.O>[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH2:30][CH2:29][C:28]1[CH:32]=[CH:33][C:34]2[O:35][CH2:24][O:25][C:26]=2[CH:27]=1)#[N:2]

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 122072243,4-Methylenedioxyphenethyl bromideHCID 199701912-(3-Cyano-3,3-diphenylpropyl)piperidine

Produkt 1

HCID 199701872-(3-Cyano-3,3-diphenylpropyl)-1-(3,4-methylenedioxyphenethyl)piperidineAusbeute 9,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-(3-cyano-3,3-diphenylpropyl)piperidine (217 mg, 0.74 mmol--see Preparation 18), 3,4-methylenedioxyphenethyl bromide (186 mg, 0.82 mmol--see Preparation 12), potassium carbonate (1.0 g) and sodium iodide (20 mg) in acetonitrile (10 ml) was heated under reflux for 48 hours, allowed to cool to room temperature and diluted with ethyl acetate and water. The organic layer was dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (31 mg, 9%) as a colourless oil, which was characterised as containing 0.75 of an equivalent of water.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by chromatography on silica
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e25de71c0b26490493a691aea975216d
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607950

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