Methyl iodide → HCID 13281071, compound

HRID 648655Notes

Reaction equation

HRID 648655 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:6]([CH:29]=1)[CH:7]([NH:14][C:15]([CH2:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Na+].[CH3:38]I>CN(C)C=O>[CH3:38][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)=[C:6]([CH:29]=1)[CH:7]([NH:14][C:15]([CH2:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1)=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20145243HCID 20145243, compound

Product 1

HCID 13281071HCID 13281071, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Four hundred seventy-two milligrams (1 m mol) of ethyl 4-[N-(5-hydroxy-α-phenyl-2-piperidino-benzyl)-aminocarbonylmethyl]-benzoate were dissolved in 25 ml of absolute dimethylformamide. After addition of 50 g of 50% sodium hydride, the mixture was stirred for 30 minutes. Then, 0.5 gm of methyl iodide were added dropwise, and the resulting mixture was stirred overnight. To work the mixture up, it was poured onto ice-water and extracted with methylene chloride. The concentrated extracts were purified by column chromatography on silica gel by use of toluene/ethyl acetate (4:1) as eluant.

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. additionTo work the mixture up, it was poured onto ice-water
  3. extractionextracted with methylene chloride
  4. customThe concentrated extracts were purified by column chromatography on silica gel by use of toluene/ethyl acetate (4:1) as eluant

Sources & evidence

ORD record
ord-9a97c6c4e8494f49aa367212c7d4c539
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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