Sodium cyanoborohydride → Benzenemethanamine, 4-fluoro-N-methoxy-

HRID 2214542Notes

Reaction equation

HRID 2214542 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[F:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][NH:3][O:2][CH3:1])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 539632384-Fluoro-benzaldehyde O-methyl-oxime

Product 1

HCID 12147060Benzenemethanamine, 4-fluoro-N-methoxy-Yield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

In an alternative procedure a solution of 4-fluorobenzaldehyde O-methyloxime (0.82 g, 5.35 mmol) in acetic acid (8 ml) was treated at 10° C. with sodium cyanoborohydride (0.67 g, 10.7 mmol) added in small portions over 10 min and the resulting solution was stirred at 25° C. for 18 h. The solvent was evaporated under reduce pressure (co-evaporation with toluene twice) and the residue was slurried with water and the pH was adjusted to 9 with 2 N aqueous sodium hydroxide. The aqueous phase was extracted twice with ether and the combined organic extracts were washed with brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residual oil was chromatographed on silica gel (elution hexane-ethyl acetate, 8:2) and distilled in vacuo to give 0.62 g (75% yield) of the title amine as a clear oil.

Workup

  1. additionadded in small portions over 10 min
  2. customThe solvent was evaporated
  3. extractionThe aqueous phase was extracted twice with ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe residual oil was chromatographed on silica gel (elution hexane-ethyl acetate, 8:2)
  8. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-7e63ac3149dd463da21c3984ff4eb9ff
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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