Pyridine → HCID 14792250, compound

HRID 1613169Notes

Reaction equation

HRID 1613169 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:24])[CH2:17][S:18]([CH2:21][CH2:22][OH:23])(=[O:20])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1[CH:33]=[CH:32]C=CC=1.[Na+].[Cl-].C(=O)([O-])[OH:37].[Na+]>C(OC(=O)C)(=O)C.C(O)(=O)C.CO.C(Cl)(Cl)Cl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:24])[CH2:17][S:18]([CH2:21][CH2:22][O:23][C:32](=[O:37])[CH3:33])(=[O:20])=[O:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 14792234HCID 14792234, compound

Product 1

HCID 14792250HCID 14792250, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 7918Acetic AnhydrideSolvent

Procedure

897 mg of N-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-(2-hydroxyethylsulfonyl)acetamide obtained in Example 7 was dissolved in 428 mg of acetic anhydride and 462 mg of pyridine and stirred at external temperature of 55° C. for 2 hours. Then, it was added to a mixture of 20 ml saturated aqueous NaCl solution and 15 ml saturated aqueous sodium hydrogencarbonate solution and was extracted with chloroform. The extracted solution was dried over magnesium sulfate, and then chloroform was distilled off under reduced pressure to obtain an oily substance. The thus obtained substance was subjected to silica gel column chromatography (solvent; chloroform:methanol=4:1). As a result, 583 mg of light brown oily N-[3-[3-(piperidinomethyl)phenoxy]propyl]-2-(2-acetoxyethylsulfonyl)acetamide containing a slight quantity of acetic acid was obtained.

Workup

  1. extractionwas extracted with chloroform
  2. dry with materialThe extracted solution was dried over magnesium sulfate
  3. distillationchloroform was distilled off under reduced pressure
  4. customto obtain an oily substance

Sources & evidence

ORD record
ord-61f6316809a749bca972b6f412764581
Source dataset
uspto-grants-1993_03
Patent number
US05192774

Reaction notes

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