Sodium Hydroxide → 3-Methylamino-1-phenylpropanol

HRID 1761285Notes

Reaction equation

HRID 1761285 reaction equation
[BH4-].[Na+].[CH3:3][NH:4][CH:5]=[CH:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[OH-].[Na+]>C(O)(=O)C>[CH3:3][NH:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2751242HCID 2751242, compoundHCID 4311764Sodium borohydride

Product 1

HCID 27339893-Methylamino-1-phenylpropanolYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In brief, exemplary methods include sodium borohydride (800 mg, 21.0 mmol) added in portions to a vigorously stirred solution of 3-methylamino-1-phenyl-2-propen-1-one (600 mg, 3.7 mmol) in glacial acetic acid (15 ml) over a period of 30 minutes at 5 to 10° C. The reaction mixture was stirred for another 30 minutes at the same temperature, and then for 3 hours at room temperature. Work up was done using 4 M aqueous sodium hydroxide (60 ml) that was added dropwise under cooling (water/ice bath). The resulting mixture was extracted with ethyl acetate (3 times 70 ml), washed with water (50 ml), and dried (Na2SO4). Evaporation of the solvent under reduced pressure gave 470 mg (77%) of 3-methylamino-1-phenyl-1-propanol as yellow oil.

Workup

  1. waitfor 3 hours at room temperature
  2. additionwas added dropwise
  3. extractionThe resulting mixture was extracted with ethyl acetate (3 times 70 ml)
  4. washwashed with water (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-3eeb5fa917824592a27f8f3520f933fc
Source dataset
uspto-grants-2005_01
Patent number
US06846957B2

Reaction notes

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