Water → Bis(2,4-dimethoxybenzyl)amine

HRID 570710Notes

Reaction equation

HRID 570710 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH:17]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(O)C>[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 691752,4-DimethoxybenzaldehydeHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 88696Bis(2,4-dimethoxybenzyl)amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,4-dimethoxybenzylamine (8.98 mL) and 2,4-dimethoxybenzaldehyde (9.94 g) in ethanol (200 mL) was stirred at room temperature for 2 hr. To the reaction mixture was added sodium triacetoxyborohydride (20.3 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8233ca0ddd084cbfbc605c26463c8098
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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