Sodium hydride → 3-[2-(4-Piperidyl)ethyl]benzonitrile hydrochloride

HRID 605790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605790
[H-].[Na+].[Br-].[C:4]([C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:5].[CH:32]([CH:34]1[CH2:39][CH2:38][N:37](C(OC(C)(C)C)=O)[CH2:36][CH2:35]1)=O.[H][H].[ClH:49].CCOC(C)=O>CCOC(C)=O.[C].[Pd].CN(C=O)C>[ClH:49].[NH:37]1[CH2:38][CH2:39][CH:34]([CH2:32][CH2:9][C:8]2[CH:7]=[C:6]([CH:31]=[CH:30][CH:29]=2)[C:4]#[N:5])[CH2:35][CH2:36]1

Komponenten

9

Edukt 5

HCID 24758Sodium hydrideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 2778355(3-Cyanobenzyl)triphenylphosphonium bromideHCID 21866389Hydrogen chloride-ethyl acetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 574218243-[2-(4-Piperidyl)ethyl]benzonitrile hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel3×

Versuchsvorschrift

Under ice cooling, sodium hydride (60% oil, 141 mg) was added to a DMF (20 ml) solution of (3-cyanobenzyl)(triphenyl)phosphonium bromide (1.6 g) and tert-butyl 4-formyl-1-piperidinecarboxylate (0.75 g), followed by stirring overnight at room temperature. The reaction liquid was diluted with EtOAc, washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=6:1 (v/v)) to obtain an oil. 10% Palladium-carbon (100 mg) was added to an EtOAc (30 ml) solution of the resulting oil, followed by stirring in a hydrogen stream atmosphere for 2 hours. The catalyst was removed with Celite, and the solvent was concentrated to obtain an oil. The resulting oil was dissolved in EtOAc (10 ml), and 4 M hydrogen chloride/EtOAc solution (5 ml) was added thereto, then stirred at room temperature for 6 hours, and then concentrated. The resulting solid was washed with ether and dried under reduced pressure to obtain 3-[2-(4-piperidinyl)ethyl]benzonitrile hydrochloride (506 mg).

Aufarbeitung

  1. customThe reaction liquid
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=6:1 (v/v))
  6. customto obtain an oil
  7. customThe catalyst was removed with Celite
  8. concentrationthe solvent was concentrated
  9. customto obtain an oil
  10. stirringstirred at room temperature for 6 hours
  11. concentrationconcentrated
  12. washThe resulting solid was washed with ether
  13. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4995f3c07649454e9338ea37452499e6
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915261B2

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