Benzaldehyde → N-[3-(Dimethoxymethyl)phenyl]benzenemethanamine

HRID 2254426Notes

Reaction equation

HRID 2254426 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1C=CC=CC=1>[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 2325713-(dimethoxymethyl)aniline

Product 1

HCID 19744680N-[3-(Dimethoxymethyl)phenyl]benzenemethanamineYield 87.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

334 mg of 3-aminobenzaldehyde dimethyl acetal was dissolved in 10 ml of anhydrous benzene, and 212 mg of benzaldehyde and 2 g of molecular sieve 4A (a product of Nippon Chromato Kogyo Co., Ltd.) were added. The mixture was stirred at room temperature for 4 hours. The molecular sieve was removed by filtration, and the filtrate was evaporated under reduced pressure. The residue was dissolved in 20 ml of methanol, and 100 mg of sodium borohydride was added. The mixture was stirred for 2 hours. The reaction mixture was diluted with water, and extracted with ethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was recrystallized from hexane to give 451 mg (yield 87.7%) of 3-benzylaminobenzaldehyde dimethyl acetal having a melting point of 55° to 56° C.

Workup

  1. addition) were added
  2. customThe molecular sieve was removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in 20 ml of methanol
  5. addition100 mg of sodium borohydride was added
  6. stirringThe mixture was stirred for 2 hours
  7. additionThe reaction mixture was diluted with water
  8. extractionextracted with ethyl ether
  9. dry with materialThe extract was dried over anhydrous sodium sulfate
  10. customthe solvent was evaporated
  11. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-e5178b211377470b899238a8a94eef08
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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