Potassium Carbonate → 4-Cyano-4-phenylpiperidine propylamine

HRID 322152

Reaktionsgleichung

Reaktionsgleichung von HRID 322152
Cl.[C:2]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#[N:3].[OH-].[Na+].Br.Br[CH2:20][CH2:21][CH2:22][NH2:23].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[NH2:23][CH2:22][CH2:21][CH2:20][N:7]1[CH2:6][CH2:5][C:4]([C:2]#[N:3])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 787013-Bromopropylamine hydrobromideHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochloride

Produkt 1

HCID 98377104-Cyano-4-phenylpiperidine propylamineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4-cyano-4-phenylpiperidine hydrochloride (5.01 g, 22.5 mmol, 1.00 equiv, Aldrich) was added to water (100 mL), and the solution was basified to pH 10-11 by addition of 6N aqueous NaOH. The aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. To the residue were added 3-bromopropylamine hydrobromide (4.92 g, 22.5 mmol, 1.00 equiv, Aldrich), anhydrous K2CO3 (3.42 g, 24.8 mmol, 1.10 equiv), and 1,4-dioxane (100 mL). The mixture was stirred at reflux for 24 hours under a CaSO4 drying tube. The solvent was removed, and the product was purified by flash chromatography (SiO2, CHCl3—MeOH-methanolic ammonia (2M) 100:8:4 to 100:20:8) to give 3.23 g (59%) of colorless oil, which was characterized spectroscopically.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with CH2Cl2 (3×100 mL)
  2. dry with materialThe combined organic solutions were dried over MgSO4
  3. concentrationconcentrated
  4. temperatureat reflux for 24 hours under a CaSO4 drying tube
  5. customThe solvent was removed
  6. customthe product was purified by flash chromatography (SiO2, CHCl3—MeOH-methanolic ammonia (2M) 100:8:4 to 100:20:8)

Quellen und Nachweise

ORD-Eintrag
ord-5ad03702a6a347498ba9e1ba3a1f4ebc
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211198B1

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