Potassium Carbonate → 3-(Dimethylamino)-1-phenylpropan-1-ol

HRID 2255080Notes

Reaction equation

HRID 2255080 reaction equation
Cl.[CH3:2][N:3]([CH3:14])[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7].C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CO.O>[CH3:14][N:3]([CH3:2])[CH2:4][CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 928441-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)HCID 4311764Sodium borohydride

Product 1

HCID 1106653-(Dimethylamino)-1-phenylpropan-1-olYield 65.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 313.7 g of 3-dimethylaminopropiophenone hydrochloride in 750 ml of methanol and 375 ml of water was added a saturated solution of potassium carbonate until the pH of the solution was 10. The solution was cooled to 0° C. by means of an external ice bath at which time 27.8 g of sodium borohydride were added in portions over a 4-hour period. The ice bath was removed and the reaction mixture stirred at room temperature overnight. The methanol was removed in vacuo and the resulting solution diluted with water and extracted four times with diethyl ether. The combined ether extracts were washed once with water, once with a saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo to provide an oil. The oil was taken up in 300 ml of hexanes and chilled overnight. The resulting crystals were recovered by filtration providing 172 g of desired subtitle intermediate as a white crystalline solid, m.p.=45°-46° C.

Workup

  1. additionwere added in portions over a 4-hour period
  2. customThe ice bath was removed
  3. customThe methanol was removed in vacuo
  4. additionthe resulting solution diluted with water
  5. extractionextracted four times with diethyl ether
  6. washThe combined ether extracts were washed once with water, once with a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto provide an oil
  10. temperaturechilled overnight
  11. filtrationThe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-44fca4e0610445779b8ee78e18c0e331
Source dataset
uspto-grants-1993_08
Patent number
US05238959

Reaction notes

Loading…