Tetrahydrofuran → N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine

HRID 622574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622574
[CH3:1][N:2]([CH3:18])[C:3]([CH:5]1[CH2:9][C:8](=O)[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=O.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:1][N:2]([CH3:18])[CH2:3][CH:5]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 14280891N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 14280892N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamineAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 2.91 g (11.8 mmol) N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide and 15 ml anhydrous tetrahydrofuran was dropped into a suspension of 1.41 g (35 mmol) lithium aluminum hydride and 30 ml tetrahydrofuran. The reaction was refluxed overnight then cooled to room temperature. To the solution was added 1.5 ml water, 1.5 ml 15% sodium hydroxide and 4.5 ml of water. The resulting precipitate was filtered. The filtrate was concentrated under reduced pressure, dissolved in dichlromethane, dried over magnesium sulfate and the solvent evaporated under reduced pressure. The residue was bulb to bulb distilled giving 1.5 g (58%) of N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine as a clear liquid. This material was used in the next step.

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight
  2. filtrationThe resulting precipitate was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutiondissolved in dichlromethane
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated under reduced pressure
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-b5433fbb7fc64a2494cfd5192eec41ca
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04771054

Notizen zur Reaktion

Wird geladen…