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

HRID 2110249Notes

Reaction equation

HRID 2110249 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-38c6be2a5f8548f9975fc9d3dcc3fa32
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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