Potassium Iodide → 5-(Piperidin-1-yl)pentan-1-amine

HRID 722684

Reaktionsgleichung

Reaktionsgleichung von HRID 722684
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>C(O)C.O1CCCC1.O>[N:7]1([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

10

Edukt 6

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 804745-ChlorovaleronitrileHCID 21226445Aluminium lithium hydrideHCID 86594854HCID 86594854, Verbindung

Produkt 1

HCID 71384475-(Piperidin-1-yl)pentan-1-amineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Chlorovaleronitrile (10 mmol), 20 mmol of piperidine, 20 mmol of potassium carbonate and a catalytic amount of potassium iodide in 50 ml of ethanol were refluxed for 6 hours. The solvent was removed under reduced pressure, the residue suspended in water and extracted with methylene chloride. The organic layer was purified by column chromatography on silica gel using methylene chloride/methanol/aqueous ammonia (90/10/1) as eluent (Yield: 59%). The product was added dropwise to a suspension of 25 mmol of lithium aluminium hydride in 25 ml of dry tetrahydrofurane at 0° C. After refluxing for 1 hour 10 ml of a saturated solution of sodium/potassium tartrate in water was added dropwise. The residue was filtered off and the filtrate purified by column chromatography on silica gel using methylene chloride/methanol/aqueous ammonia (90/10/1) as eluent. The residue was crystallized with hydrochloric acid from diethyl ether/2-propanol.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with methylene chloride
  3. customThe organic layer was purified by column chromatography on silica gel
  4. additionwas added dropwise
  5. filtrationThe residue was filtered off
  6. customthe filtrate purified by column chromatography on silica gel
  7. customThe residue was crystallized with hydrochloric acid from diethyl ether/2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-808c0d510de1419c965e2e9d99b9ad1e
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138413B1

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