Benzaldehyde → HCID 28435578, compound

HRID 1174505Notes

Reaction equation

HRID 1174505 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][CH:5]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+]>CCO>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:5]=1)=[O:12]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 571728Methyl 4-(aminomethyl)benzoateHCID 4311764Sodium borohydride

Product 1

HCID 28435578HCID 28435578, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl-4-(aminomethyl)benzoate (50 g, 0.302 mol) and benzaldehyde (32 g, 0.302 mol) in EtOH (1 L) was refluxed for 5 h. After cooling to r.t, NaBH4 (11.5 g, 0.302 mol) was added portionwise. The reaction mixture was stirred at r.t. for 10 h. The solvent was removed under reduced pressure and the compound was purified by acid-base work up to give N-(4-methoxycarbonylbenzyl)benzylamine (25 g, 33%).

Workup

  1. temperaturewas refluxed for 5 h
  2. temperatureAfter cooling
  3. customThe solvent was removed under reduced pressure
  4. customthe compound was purified by acid-base work up

Sources & evidence

ORD record
ord-49663c2578b34ecb92f578a24c46772b
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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