Water → N-[1-(3-Dimethylaminopropyl)piperidin-4-yl]-N-methylamine

HRID 492911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492911
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=O)OC(C)(C)C)[CH2:9][CH2:8]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:7]1[CH2:8][CH2:9][CH:10]([NH:13][CH3:14])[CH2:11][CH2:12]1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57677405Tert-butyl[1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate

Produkt 1

HCID 23153255N-[1-(3-Dimethylaminopropyl)piperidin-4-yl]-N-methylamineAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of tert-butyl [1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate (2.73 g) in tetrahydrofuran (30 ml) was stirred in an ice bath, and lithium aluminum hydride (1.04 g) was gradually added thereto. The mixture was stirred under a nitrogen atmosphere, for 15 minutes in an ice bath and for 15 minutes at room temperature. It was further heated to reflux for 7 hours under a nitrogen atmosphere. The reaction mixture was cooled in an ice bath, and then water (1.0 ml), 5N aqueous sodium hydroxide (1.0 ml) and water (5.0 ml) were added thereto in that order and stirring was carried out on ice. The insoluble portion was filtered. The filtrate was concentrated to provide the title compound (1.51 g, 83.2%) as a pale yellow oil.

Aufarbeitung

  1. temperatureIt was further heated
  2. temperatureto reflux for 7 hours under a nitrogen atmosphere
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. stirringin that order and stirring
  5. filtrationThe insoluble portion was filtered
  6. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-71ddb3b7d94949dfad61232b0f225c7d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531532B2

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