Red-Al → (3-Benzylphenyl)methanamine

HRID 1264681Notes

Reaction equation

HRID 1264681 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCO[AlH2-]OCCOC.[Na+].[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][NH2:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 222388273-(Benzyl)benzamide

Product 1

HCID 22312794(3-Benzylphenyl)methanamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(benzyl)benzamide (0.0094 moles) from Step B in 70 of toluene was added 8 mL of Red-Al® (65+wt. % solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene, Aldrich) (CAUTION—reaction very exothermic). The reaction mixture was then heated at 60° C. for 2 hours and then poured over ice. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with water and brine. The organic layer was extracted with 1N HCl and the aqueous layer washed with ethyl acetate. The pH of the aqueous layer was then adjusted to about 9.0 with 1N NaOH and extracted with ethyl acetate. The organic extracts were washed with water and brine and then concentrated to give 3-(benzyl)benzyl amine.

Workup

  1. additionpoured over ice
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe combined extracts were washed with water and brine
  4. extractionThe organic layer was extracted with 1N HCl
  5. washthe aqueous layer washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe organic extracts were washed with water and brine
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0fc301f746db47bf80e4dcf5900e2185
Source dataset
uspto-grants-2003_04
Patent number
US06544978B2

Reaction notes

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