4-Morpholinobenzonitrile → 4-Morpholinobenzylamine

HRID 585994

Reaction equation

HRID 585994 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][NH2:12])=[CH:13][CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3948084-MorpholinobenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 27764584-Morpholinobenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Morpholinyl)benzonitrile (1.24 g, 6.6 mmol) in THF (25 mL) at 0° C. was treated with LiAlH4 (2.5 g, 65.9 mmol) and refluxed for 1 hour. The mixture was cooled to room temperature and quenched by careful addition of 1N NaOH and then H2O. The mixture was concentrated, extracted with diethyl ether. The combined ethereal extracts were washed with saturated NaHCO3 solution, dried over Na2SO4, and evaporated in vacuo to provide the title compound which was dried over MgSO4 as a THF:diethylether solution before the next step.

Workup

  1. temperaturerefluxed for 1 hour
  2. customquenched by careful addition of 1N NaOH
  3. concentrationThe mixture was concentrated
  4. extractionextracted with diethyl ether
  5. washThe combined ethereal extracts were washed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-979ec15a92dc408899029fd55e65e1d4
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Linked notes

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