Acetic Acid → 1-(2-Fluoro-5-methoxyphenyl)-N,N-dimethylmethanamine

HRID 1178529Notes

Reaction equation

HRID 1178529 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[CH3:12][NH:13][CH3:14].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][N:13]([CH3:14])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 27348722-Fluoro-5-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 219304071-(2-Fluoro-5-methoxyphenyl)-N,N-dimethylmethanamineYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Fluoro-5-methoxybenzaldehyde (2.62 g, 17.0 mmol), dimethylamine (2M in methanol, 17 mL, 34 mmol) and sodium cyanoborohydride (1.17 g, 18.7 mmol) were stirred at ambient temperature in a solution of glacial acetic acid (2 mL) in methanol (100 mL) for 66 h. The solvent was removed in vacuo. The residue was treated with 10% sodium carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was washed with water (2×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to give (2-fluoro-5-methoxybenzyl)dimethylamine (3.02 g, 97%) as a yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water (2×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-85e32466cf34451ba49b23abd91a7f86
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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