Benzylamine → Ethyl 2-(benzylamino)propanoate

HRID 408576

Reaction equation

HRID 408576 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH:5](Br)[CH3:6])[CH3:2].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:8])[CH:5]([NH:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:6])[CH3:2]

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 222273Ethyl 2-(benzylamino)propanoate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-bromo-propionic acid ethyl ester (1 eq.) in MeCN was added benzylamine (0.9 eq.) and potassium carbonate (1.5 eq.). The reaction was refluxed for 4 h then cooled to 20° C. and diluted with EtOAc. The crude was filtered, the filtrate was concentrated under reduced pressure, then purified by chromatography on silica gel (elution with heptane/EtOAc: 7/3) to afford 2-benzylamino-propionic acid ethyl ester.

Workup

  1. temperatureThe reaction was refluxed for 4 h
  2. filtrationThe crude was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. custompurified by chromatography on silica gel (elution with heptane/EtOAc: 7/3)

Sources & evidence

ORD record
ord-fc45d469a0f844739eca3e6cf59e1fff
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Linked notes

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