Benzaldehyde → Dibenzylamine

HRID 1502930Notes

Reaction equation

HRID 1502930 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)=O>[Ir].CO>[CH2:1]([NH:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 284Formic AcidHCID 7504Benzylamine

Product 1

HCID 7656Dibenzylamine

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Under an argon-gas atmosphere, 5 mL of dehydrated methanol, 505 μL (5.0 mmol) of benzaldehyde (MW: 106.12), 545 μL (5.0 mmol) of benzylamine (MW: 107.15), 566 μL (15.0 mmol) of formic acid (MW: 46.43), and 5.90 mg (0.01 mmol, S/C=500) of the iridium catalyst Ir-7 (MW: 590.13) were introduced in a 20-mL Schlenk tube, and the mixture was stirred while heating at 60° C. for 1.5 hr. After distillation of the solvent, a saturated sodium hydrogen carbonate solution was added, then a product was extracted with methylene chloride, the organic layer was washed with water, and the product was dried with sodium sulfate. The drying agent was removed by filtration and the methylene chloride was distilled away to give a crude product dibenzylamine. Its conversion rate was 100% based on NMR measurement, with 95% of dibenzylamine, 3% of tribenzylamine, and 2% of benzyl alcohol.

Workup

  1. distillationAfter distillation of the solvent
  2. additiona saturated sodium hydrogen carbonate solution was added
  3. extractiona product was extracted with methylene chloride
  4. washthe organic layer was washed with water
  5. dry with materialthe product was dried with sodium sulfate
  6. customThe drying agent was removed by filtration
  7. distillationthe methylene chloride was distilled away

Sources & evidence

ORD record
ord-1e71bb293d284e399d2593d458179be2
Source dataset
uspto-grants-2015_12
Patent number
US09211533B2

Reaction notes

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