Water → Methyl 4-({[2-(5-fluoro-2-methoxyphenyl)ethyl]amino}methyl)benzoate

HRID 505608Notes

Reaction equation

HRID 505608 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH2:8][CH2:9][N:10]=[CH:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)[CH:7]=1.[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22014991Methyl 4-({[2-(5-fluoro-2-methoxyphenyl)ethyl]imino}methyl)benzoate

Product 1

HCID 22015000Methyl 4-({[2-(5-fluoro-2-methoxyphenyl)ethyl]amino}methyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.30 g (16.8 mmol) of methyl 4-({[2-(5-fluoro-2-methoxyphenyl)ethyl]imino}-methyl)benzoate are dissolved in 48.4 ml of methanol, and 1.27 g (33.6 mmol) of sodium borohydride are added. The solution is stirred at RT for 2 hours, and water is then added and the solution is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is taken up in ethyl acetate and extracted with diluted HCl. The aqueous phase is made alkaline and extracted with ethyl acetate, and the extract is dried over magnesium sulphate, filtered and concentrated under reduced pressure.

Workup

  1. extractionthe solution is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted with diluted HCl
  6. extractionextracted with ethyl acetate
  7. dry with materialthe extract is dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e16a872ad0f4b21ae3d900e4bf24742
Source dataset
uspto-grants-2010_08
Patent number
US07781470B2

Reaction notes

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