Benzoyl chloride → HCID 54569884, compound

HRID 847740Notes

Reaction equation

HRID 847740 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][OH:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][O:18][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 91276Roxatidine

Product 1

HCID 54569884HCID 54569884, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

150 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydroxyacetamide was dissolved in 0.5 ml of pyridine, and 150 mg of benzoyl chloride was added dropwise to the solution under ice cooling. After the addition, the mixture was stirred at room temperature for 2 hours. The solvent was distilled off and water was added. The mixture was alkalized with aqueous ammonia, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was separated and purified by TLC (developing solvent: chloroform/methanol=19/l) to afford 165 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]benzoyloxyacetamide.

Workup

  1. additionAfter the addition
  2. distillationThe solvent was distilled off
  3. additionwater was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was separated
  8. custompurified by TLC (developing solvent: chloroform/methanol=19/l)

Sources & evidence

ORD record
ord-b6eef20fd2ef43d0b3017faef5ebed17
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

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