Ammonium Chloride → 2-(1-Benzhydrylazetidin-3-YL)ethanamine

HRID 1450716

Reaktionsgleichung

Reaktionsgleichung von HRID 1450716
[C:1]([CH2:3][CH:4]1[CH2:7][N:6]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[NH4+].[Cl-]>C1COCC1>[NH2:2][CH2:1][CH2:3][CH:4]1[CH2:7][N:6]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5]1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 222576333-Cyanomethyl-1-benzhydryl azetidine

Produkt 1

HCID 222576342-(1-Benzhydrylazetidin-3-YL)ethanamineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5.7 g (21.7 mmol) of 3-cyanomethyl-1-benzhydryl azetidine was added slowly to a suspention of 2.9 g (76.0 mmol) of LiAlH4 in 80 mL of dry THF at roomtemperature. The reaction mixture was refluxed for 4 h. Excess hydride reagent was hydrolyzed by careful addition, with cooling, of NH4Cl(aq), the gelatinous mixture was filtered and the filter cake was washed repeatedly with THF. The solvent was evaporated, the residue was dissolved in diethyl ether, washed with brine and dried with Na2SO4. Evaporation of the solvent gave 5.0 g (87%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. filtrationthe gelatinous mixture was filtered
  3. washthe filter cake was washed repeatedly with THF
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in diethyl ether
  6. washwashed with brine
  7. dry with materialdried with Na2SO4
  8. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-f20ba4c75f27440790051abe89c8629f
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602253

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