Potassium Carbonate → HCID 60795277, compound

HRID 1187648Notes

Reaction equation

HRID 1187648 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:10]1([NH2:13])[CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:10]1([NH:13][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 69828Cyclopropylamine

Product 1

HCID 60795277HCID 60795277, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a 250 mL of sealed tube was added ethyl 2-bromo-2-methylpropanoate (19.4 g, 0.1 mol, 1.0 equiv), cyclopropanamine (11.4 g, 0.2 mol, 2.0 equiv), K2CO3 (27.6 g, 0.2 mol, 2.0 equiv), KI (1.66 g, 0.01 mol, 0.1 equiv) and 200 mL of MeCN. The mixture was stirred at 100° C. for 12 h then cooled to room temperature and the solids were filtered. The filtrate was concentrated and purified on silica gel column eluting with pet. ether/ethyl acetate=4/1 to give 8.0 g (46%) of ethyl 2-(cyclopropylamino)-2-methylpropanoate.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationthe solids were filtered
  3. concentrationThe filtrate was concentrated
  4. custompurified on silica gel column
  5. washeluting with pet. ether/ethyl acetate=4/1

Sources & evidence

ORD record
ord-65832dd9e5ed447da552c26450237ad4
Source dataset
uspto-grants-2014_03
Patent number
US08673925B1

Reaction notes

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