Water → Methyl 2-(methylamino)-2-phenylacetate

HRID 3974

Reaction equation

HRID 3974 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[Cl-].[CH3:14][NH3+:15].C(=O)(O)[O-].[Na+].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH3:14][NH:15][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 11637Methanamine, hydrochloride (1:1)HCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 13852358Methyl 2-(methylamino)-2-phenylacetateYield 71.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

In this example a mixture containing 30.7 g of methyl bromo-phenylacetate, 36.2 g of methyl ammonium chloride (i.e. CH3NH3Cl); 3.0 g of benzyltriethylammonium chloride and 67.5 g of sodium bicarbonate in about 300 ml of methylene chloride (and about 25 ml of water) was warmed to refluxed and refluxed for about 18 hours. The mixture was then cooled and washed three times with water, dried over magnesium sulfate and concentrated by vacuum evaporation affording 17.1 g of the title compound as an oil.

Workup

  1. temperatureto refluxed
  2. temperaturerefluxed for about 18 hours
  3. temperatureThe mixture was then cooled
  4. washwashed three times with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by vacuum evaporation

Sources & evidence

ORD record
ord-c156814239954cc794d18661347d1e7d
Source dataset
uspto-grants-1988_02
Patent number
US04723031

Linked notes

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