2,4-Dimethoxybenzylamine → HCID 90460239, compound

HRID 588759Notes

Reaction equation

HRID 588759 reaction equation
[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=O.[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].[BH4-].[Na+]>CO.C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7][NH:18][CH2:17][C:16]1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=1[O:14][CH3:13]

Participants

5

Reactant 3

HCID 5972502,4-DimethoxybenzylamineHCID 4311764Sodium borohydrideHCID 10634380HCID 10634380, compound

Product 1

HCID 90460239HCID 90460239, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The solution of 5-bromo-4-chloro-2-methoxybenzaldehyde (300 mg, 1.2 mmol) and 2,4-dimethoxybenzyl amine (167 mg, 1.2 mmol) in MeOH/DCM (4:1, 10 mL) was stirred at room temperature for 5 h. To this mixture, NaBH4 (100 mg, 13 mmol) was added in two portions. The mixture stirred for 1 h and then partitioned between DCM and water. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the desired product. The crude product was used directly in the next step without further purification.

Workup

  1. custompartitioned between DCM and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e979077cbe664494808b7c9c5811bc75
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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