4-Phenylbenzamide → 4-Phenylbenzylamine

HRID 480741Notes

Reaction equation

HRID 480741 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([NH2:9])=O)=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:10]1([C:1]2[CH:2]=[CH:3][C:4]([CH2:7][NH2:9])=[CH:5][CH:6]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6025064-PhenylbenzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 3449894-Phenylbenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-biphenylcarboxamide (Aldrich) (0.025 mole) in 150 mL of THF cooled to 10° C. was added a solution of 1.5 eq of LAH (1M in THF) dropwise. The reaction mixture turned from a white slurry to a green homogenous solution and then to a yellow homogeneous solution. The reaction was then quenched with 2.5 mL of 1N NaOH. The mixture was then filtered through Hyflo and extracted with ethyl acetate. The organic layer was then washed with 1N HCl. The pH of the resulting aqueous layer was adjusted to about 9 with 1N NaOH and extracted with ethyl acetate. The organic extracts were washed with water and brine, and then dried over Na2SO4, filtered and concentrated to give 4-(phenyl)benzyl amine as a white solid.

Workup

  1. customThe reaction was then quenched with 2.5 mL of 1N NaOH
  2. filtrationThe mixture was then filtered through Hyflo
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was then washed with 1N HCl
  5. extractionextracted with ethyl acetate
  6. washThe organic extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8a5ba4b9700c425385334f4cad767bcb
Source dataset
uspto-grants-2003_11
Patent number
US06653303B1

Reaction notes

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