Water → HCID 12780079, compound

HRID 847741Notes

Reaction equation

HRID 847741 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.[H-].[Na+].[CH3:25]I.O>CN(C)C=O>[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][CH3:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 91276Roxatidine

Product 1

HCID 12780079HCID 12780079, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 645 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]hydroxyacetamide in 2 ml of N,N-dimethylformamide was added under ice cooling to a suspension of 84.3 mg of sodium hydride in 1 ml of N,N-dimethylformamide, and the mixture was stirred for 5 minutes. Then, a solution of 299.3 mg of methyl iodide in 1 ml of N,N-dimethylformamide was added dropwise under ice cooling, and the mixture was stirred for 10 minutes. After the stirring, water was added, and the mixture was 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 250 mg of N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]methoxyacetamide.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was separated
  6. custompurified by TLC (developing solvent: chloroform/methanol=19/l)

Sources & evidence

ORD record
ord-b96c77cd710c4d088d88841aa5586ca9
Source dataset
uspto-grants-1981_10
Patent number
US04293557

Reaction notes

Loading…