Potassium Carbonate → Methyl 2-{[(4-chlorophenyl)methyl]amino}acetate

HRID 408583Notes

Reaction equation

HRID 408583 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12](=[O:15])[CH2:13]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:10][O:11][C:12](=[O:15])[CH2:13][NH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 660364-Chlorobenzylamine

Product 1

HCID 19082816Methyl 2-{[(4-chlorophenyl)methyl]amino}acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4-chloro-benzylamine (1 eq.) in MeCN was added bromo-acetic acid methyl ester (1 eq.), K2CO3 (1.5 eq.) and KI (0.1 eq.). The reaction was stirred for 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and EtOAc. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 8/2) to afford (4-chloro-benzylamino)-acetic acid methyl ester.

Workup

  1. concentrationThe crude was concentrated under reduced pressure
  2. customthen partitioned between water and EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 8/2)

Sources & evidence

ORD record
ord-8b5cf6148bb44d65889f30e19f8628b0
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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