Hydrochloric Acid → 1-(3-Phenyl-2-propyn-1-yl)piperidine

HRID 6792

Reaktionsgleichung

Reaktionsgleichung von HRID 6792
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:15]=O.Cl>O1CCOCC1.[Cu]Cl>[C:1]1([C:7]#[C:8][CH2:15][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 10821Phenylacetylene

Produkt 1

HCID 2007111-(3-Phenyl-2-propyn-1-yl)piperidineAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 312751,4-DioxaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

With stirring, a solution of phenylacetylene (10.2 g) in dioxane (10 ml), a solution of piperidine (13.3 g) in dioxane (10 ml) and copper(I) chloride (0.1 g) were added successively to a suspension of paraformaldehyde (3.6 g) in dioxane (10 ml). The mixture was heated under reflux for 6 hours, allowed to cool to 25° C. and acidified using 20% strength hydrochloric acid. The solution was washed with diethyl ether and the aqueous phase was made alkaline using 50% strength aqueous sodium hydroxide solution and extracted with diethyl ether (3×100 ml). The organic phase was dried with magnesium sulfate and concentrated completely. Distillation of the residue under reduced pressure gave an oil (13.0 g) of boiling point 95° C./0.045 mm Hg.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. washThe solution was washed with diethyl ether
  4. extractionextracted with diethyl ether (3×100 ml)
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. concentrationconcentrated completely
  7. distillationDistillation of the residue under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a76fbde539d14fbe965fa11a289cc844
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084158B2

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