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

HRID 1610819Notes

Reaction equation

HRID 1610819 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1ecf6b620ca145c395ebb08a7bf1fb04
Source dataset
uspto-grants-2006_01
Patent number
US06984627B1

Reaction notes

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