Methylamine → (4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine

HRID 68615

Reaction equation

HRID 68615 reaction equation
[CH3:1][NH2:2].[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1.[BH4-].[Na+]>CO>[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH2:15][NH:2][CH3:1])=[CH:13][C:12]=2[Br:19])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 230102233-Bromo-4-((4-methoxybenzyl)oxy)benzaldehyde

Product 1

HCID 63045147(4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2M methylamine in MeOH (30 mL) was added intermediate 32 (2.91 g, 9.1 mmol, 1 eq). After stirring this mixture at room temperature for 30 min, the solvent was removed and the residue was partitioned between saturated NaHCO3 and DCM (2×100 mL). The organic layer was dried (Na2SO4) and concentrated. The resultant residue was dissolved in MeOH (25 mL) and, after addition of sodium borohydride (1.0 g, 27.6 mmol, 3 eq), the mixture was stirred at room temperature for 1 h. Solvent was removed and the residue was partitioned between a Na2CO3 solution and CHCl3. The resultant organic layer was dried (Na2SO4) and concentrated in vacuo to give 2.7 g, (88%) of (4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine (33).

Workup

  1. customthe solvent was removed
  2. customthe residue was partitioned between saturated NaHCO3 and DCM (2×100 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe resultant residue was dissolved in MeOH (25 mL)
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. customSolvent was removed
  8. customthe residue was partitioned between a Na2CO3 solution and CHCl3
  9. dry with materialThe resultant organic layer was dried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e2bdbd81f0c4e6ea906aa73e3b13f53
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Linked notes

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