3-Fluoro-p-anisaldehyde → N-(2,2-Dimethoxyethyl)-3-fluoro-4-methoxybenzenemethanamine

HRID 981570Notes

Reaction equation

HRID 981570 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH2:16].[BH4-].[Na+]>C(O)C>[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH:16][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 676963-Fluoro-p-anisaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 4311764Sodium borohydride

Product 1

HCID 20070446N-(2,2-Dimethoxyethyl)-3-fluoro-4-methoxybenzenemethanamineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

3--Fluoro-4-methoxybenzaldehyde (5.0 g, 0.0324 mole) was added to aminoacetaldehyde dimethyl acetal (3.53 ml, 0.0324 mole) and the mixture was heated at 100° C. for 2 hours. The reaction mixture was cooled in ice, diluted with ethyl alcohol (50 ml) and sodium borohydride (1.23 g, 0.0324 mole) was added and the mixture was stirred overnight at 25° C. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and the solution was washed with water and brine and then dried with sodium sulfate. The mixture was filtered and the solvent removed under reduced pressure to give N-(3-fluoro-4-methoxybenzyl)-aminoacetaldehyde dimethyl acetal as an oil (6.68 g, 85%).

Workup

  1. temperatureThe reaction mixture was cooled in ice
  2. additionwas added
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water and brine
  6. dry with materialdried with sodium sulfate
  7. filtrationThe mixture was filtered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f948ea37d65c40ac9d274b94f93ce13a
Source dataset
uspto-grants-1991_02
Patent number
US04992459

Reaction notes

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