Acetic Anhydride → HCID 21545529, compound

HRID 1605902Notes

Reaction equation

HRID 1605902 reaction equation
[C:1]([CH2:4][C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[O:7][CH2:8][CH:9]([OH:25])[CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)(=[O:3])[NH2:2].[C:30](OC(=O)C)(=[O:32])[CH3:31].[OH-].[Na+]>N1C=CC=CC=1>[C:1]([CH2:4][C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[O:7][CH2:8][CH:9]([O:25][C:30](=[O:32])[CH3:31])[CH2:10][N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:15][CH2:16]1)(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 21545531HCID 21545531, compound

Product 1

HCID 21545529HCID 21545529, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Two grams of 1-(2-carbamoylmethylphenoxy)-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-2-ol are added to 20 ml. of anhydrous pyridine, followed by the immediate addition of 8.0 g. of acetic anhydride with stirring. The resulting solution is refluxed for a period of 5 minutes, cooled and subsequently poured into 50 ml. of ice water, basified with 2N aqueous sodium hydroxide solution and extracted with chloroform. The organic phase is then washed with water, dried over anhydrous sodium sulfate and evaporated to yield the crude product. After recrystallization from ethanol, there is obtained pure 1-(2-carbamoylmethylphenoxy)-3-[4-(2-methoxyphenyl)piperazin-1-yl]-2-acetoxypropane as final product.

Workup

  1. temperatureThe resulting solution is refluxed for a period of 5 minutes
  2. temperaturecooled
  3. additionsubsequently poured into 50 ml
  4. extractionextracted with chloroform
  5. washThe organic phase is then washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customto yield the crude product
  9. customAfter recrystallization from ethanol

Sources & evidence

ORD record
ord-d2cf97a576394c3491735d8d8bab1f39
Source dataset
uspto-grants-1976_04
Patent number
US03951983

Reaction notes

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