Water → 4-Morpholinobenzylamine

HRID 887192Notes

Reaction equation

HRID 887192 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].[OH-].[Na+].O>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

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 3948084-MorpholinobenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 27764584-MorpholinobenzylamineYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 66A (1.24 g, 6.6 mmol) in THF (25 mL) was treated with LiAlH4 (2.5 g, 65.9 mmol) at 0° C. The mixture was allowed to warm to room temperature and then refluxed for 1 hour. The mixture was allowed to cool to room temperature and then treated with 1N NaOH carefully followed by water. The mixture was concentrated under reduced pressure and the resulting aqueous mixture was extracted with diethyl ether. The organic extracts were combined, washed with saturated NaHCO3 solution, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure to provide the title compound as a yellow oil (286 mg, 23%).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureto cool to room temperature
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionthe resulting aqueous mixture was extracted with diethyl ether
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d154355f3749465f808bb5242786427e
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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