Ethyl bromoacetate → HCID 67315955, compound

HRID 1012566Notes

Reaction equation

HRID 1012566 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>O1CCCC1>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=1)[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15965417HCID 15965417, compound

Product 1

HCID 67315955HCID 67315955, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

13.4 g (46.6 mmol, 1.0 equivalent) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a) and 100 ml of tetrahydrofuran were charged in a 300 ml three-necked flask and dissolved. 7.76 g (56.1 mmol, 1.2 equivalents) of potassium carbonate and 8.20 g (49.1 mmol, 1.05 equivalents) of ethyl bromoacetate were added thereto at room temperature, the mixture was stirred at 60° C. for nine hours. After cooling the mixture to room temperature, salts were removed by filtration, and the solvent was concentrated. The residue was extracted with 250 ml of toluene and 250 ml of a 1N sodium hydroxide aqueous solution. The organic layer was washed with 250 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 13.2 g of 4-[(4-dipropylaminobutyl)ethoxycarbonylmethylamino]methylbenzonitrile (11) as an oily substance (yield: 76%).

Workup

  1. dissolutiondissolved
  2. temperatureAfter cooling the mixture to room temperature
  3. customsalts were removed by filtration
  4. concentrationthe solvent was concentrated
  5. extractionThe residue was extracted with 250 ml of toluene and 250 ml of a 1N sodium hydroxide aqueous solution
  6. washThe organic layer was washed with 250 ml of a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-06dbb2ca6b83494eb1f263c4d620b6d6
Source dataset
uspto-grants-2011_07
Patent number
US07977512B2

Reaction notes

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