Toluene → Bis(4-methoxybenzyl)amine

HRID 59930

Reaction equation

HRID 59930 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.[BH4-].[Na+]>O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 312444-MethoxybenzaldehydeHCID 754524-MethoxybenzylamineHCID 4311764Sodium borohydride

Product 1

HCID 714952Bis(4-methoxybenzyl)amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

p-Anisaldehyde (411 mmol), 4-methoxybenzylamine (411 mmol) and toluene (500 mL) were combined in a round bottomed flask fitted with a condenser and a Dean-Stark trap. The reaction was refluxed for 1 h during which water was removed from the reaction mixture. The reaction was cooled and concentrated. The residue was dissolved in MeOH (120 mL). The mixture was cooled to 5° C. and NaBH4 (205 mmol) was added in portions over 45 min. The reaction was slowly heated to reflux. After 2 h at reflux, the reaction was cooled to room temperature and concentrated. The residue was dissolved in EtOAc. The organic layer was washed (3×H2O and brine), dried (Na2SO4) and concentrated to yield the desired product.

Workup

  1. customfitted with a condenser
  2. customwas removed from the reaction mixture
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in MeOH (120 mL)
  6. temperatureThe reaction was slowly heated to reflux
  7. temperatureAfter 2 h at reflux
  8. temperaturethe reaction was cooled to room temperature
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in EtOAc
  11. washThe organic layer was washed (3×H2O and brine)
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-2781ce35c46f4b819672aab6953c86b7
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Linked notes

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