Ethyl bromoacetate → N-ethoxycarbonylmethyl-N-(2-ethoxycarbonylpropyl)benzylamine

HRID 358905Notes

Reaction equation

HRID 358905 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:8]([O:10][C:11]([CH:13]([CH3:23])[CH2:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:12])[CH3:9].[OH-].[Na+]>C(O)C>[CH2:6]([O:5][C:3]([CH2:2][N:15]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:14][CH:13]([C:11]([O:10][CH2:8][CH3:9])=[O:12])[CH3:23])=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 13555213Ethyl 3-(benzylamino)-2-methylpropanoate

Product 1

HCID 13933137N-ethoxycarbonylmethyl-N-(2-ethoxycarbonylpropyl)benzylamineYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

88.4 g (0.53 mole) of ethyl bromoacetate were added to a solution of 98.0 g (0.44 mole) of N-(2-ethoxycarbonylpropyl)benzylamine [prepared as described in Step (1) above] dissolved in 200 ml of ethanol, and the mixture was heated under reflux for 2 hours. The reaction mixture was then poured into 500 ml of ice-water and made alkaline by the addition of a 50% w/v aqueous solution of sodium hydroxide. It was then extracted with ethyl acetate. The ethyl acetate extract was washed, in turn, with a 1N aqueous solution of sodium hydroxide and with water and dried. It was then freed from the solvent by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 1:9 by volume mixture of ethyl acetate and toluene, to give 83.0 g of N-ethoxycarbonylmethyl-N-(2-ethoxycarbonylpropyl)benzylamine as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionIt was then extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed, in turn, with a 1N aqueous solution of sodium hydroxide and with water
  6. customdried
  7. customIt was then freed from the solvent by evaporation under reduced pressure
  8. customThe residue was purified by column chromatography through silica gel
  9. washeluted with a 1:9 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-1ea0ac5b8d514503922a77d7d1d0fcba
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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