Water → HCID 22292755, compound

HRID 966946Notes

Reaction equation

HRID 966946 reaction equation
Br[CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[CH:8]([NH2:11])([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH:8]([NH:11][CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 22292755HCID 22292755, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 2-bromopropionate (10.0 g, 59.9 mmol) was dissolved in acetonitrile (200 mL) followed by addition of isopropylamine (15.3 mL, 180 mmol), potassium carbonate (24.8 g, l80 mmol) and benzyltriethylammonium chloride (1.36 g, 5.99 mmol), and then the mixture was stirred at 70° C. for 17 hours. Water was added to the reaction mixture, and then the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and methyl 2-(isopropylamino)propionate (6.70 g; yield 77%) was thus obtained.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-e0b33554db5e48a18b9918699d1f5e58
Source dataset
uspto-grants-2005_10
Patent number
US06953785B2

Reaction notes

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