Thionyl Chloride → HCID 54044148, compound

HRID 1899839Notes

Reaction equation

HRID 1899839 reaction equation
O[CH2:2][CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.O=S(Cl)[Cl:19].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:19][CH2:2][CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 201858HCID 201858, compound2×HCID 516892Sodium Bicarbonate

Product 1

HCID 54044148HCID 54044148, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-hydroxy-3-morpholino-2-phenylpropane (650 mg, 2.94 mmol) prepared in the above (3) dissolved in dichloromethane (10 ml), SOCl2 (420 mg, 3.53 mmol) in dichloromethane (5 ml) was added while chilling with ice. After the resulting solution was stirred to cause reaction at room temperature for 23 hours, saturated aqueous sodium bicarbonate was added while chilling with ice. The prepared solution was extracted with dichloromethane, and the extract was washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure to obtain a crude product. The product was purified by silica gel column chromatography using acetone/hexane=1/5 to obtain 540 mg of the titled compound as a colorless oil (yield: 76.6%).

Workup

  1. temperaturewhile chilling with ice
  2. customreaction at room temperature for 23 hours
  3. temperaturewhile chilling with ice
  4. extractionThe prepared solution was extracted with dichloromethane
  5. washthe extract was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customSubsequently, the solvent was removed by distillation under reduced pressure
  8. customto obtain a crude product
  9. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-385204dd2d20432ea28ddbe883286206
Source dataset
uspto-grants-1996_11
Patent number
US05574030

Reaction notes

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