Methyl iodide → Methyl 4-(2-cyclohexylethylamino)phenylacetate

HRID 2166777Notes

Reaction equation

HRID 2166777 reaction equation
[CH:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:22]I>CN(C)P(N(C)C)(N(C)C)=O>[CH:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH3:22])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 204989854-(2-Cyclohexylethylamino)phenylacetic acid

Product 1

HCID 20498942Methyl 4-(2-cyclohexylethylamino)phenylacetate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A solution of 20.7 g. of 4-(2-cyclohexylethylamino)phenylacetic acid in 25 ml. of hexamethylphosphoramide is added to a stirred mixture of 0.800 g. of sodium hydride (57% in mineral oil) and 25 ml. of hexamethylphosphoramide. The solution which forms after one hour is treated with 11.0 g. of methyl iodide and is then stirred at 25° C. for 18 hours. Dilution with water followed by filtration affords a white solid which is crystallized from ethanol to yield methyl 4-(2-cyclohexylethylamino)phenylacetate.

Workup

  1. additionis treated with 11.0 g
  2. filtrationDilution with water followed by filtration
  3. customaffords a white solid which
  4. customis crystallized from ethanol

Sources & evidence

ORD record
ord-e4a6ac9362174da98996cff39302916b
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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