Isopropylamine → Ethyl 2-((propan-2-yl)amino)acetate

HRID 2368820Notes

Reaction equation

HRID 2368820 reaction equation
[CH3:1][CH:2]([NH2:4])[CH3:3].Cl[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]>C1(C)C=CC=CC=1>[CH:2]([NH:4][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 7751Ethyl chloroacetate

Product 1

HCID 351625Ethyl 2-((propan-2-yl)amino)acetateYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Propan-2-amine (2001) (59 g, 1.0 mol) and ethyl chloroacetate (122 g, 1.0 mol) were dissolved in toluene (200 mL) and the mixture was stirred at reflux for 2 h. The reaction mixture was allowed to cool to RT, poured into ice-water (500 mL) and extracted with ethyl acetate (3×250 mL). The combined organic layer was washed with brine (50 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (10-50% EA/PE) to afford the product, ethyl 2-(isopropylamino)acetate (2002) (70 g, 51% yield) as an oil.

Workup

  1. temperatureat reflux for 2 h
  2. extractionextracted with ethyl acetate (3×250 mL)
  3. washThe combined organic layer was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel (10-50% EA/PE)

Sources & evidence

ORD record
ord-e9f94d4753a74732b28dd4c5960e57f6
Source dataset
uspto-grants-2014_04
Patent number
US08703777B2

Reaction notes

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