N-Methylbenzylamine → (Benzyl-methyl-amino)-acetic acid methyl ester

HRID 480241Notes

Reaction equation

HRID 480241 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:7]

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 60984Methyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 11229312(Benzyl-methyl-amino)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl bromoacetate (10 g, 65.4 mmol, 1.0 equiv) was dissolved in 100 mL of CH2Cl2 which was then cooled to 0° C. N-Methylbenzylamine (7.92 g, 65.4 mmol, 1.0 equiv) was added dropwise over a 10 min period at which time Hunig's base (21 g, 163 mmol, 2.49 equiv) was added and the reaction was allowed to warm to room temperature and was stirred for 16 h. The reaction was diluted with 50 mL of saturated bicarbarbonate and the layers were separated. The organic layer was washed once more with 50 mL of sodium bicarbonate, dried over Na2SO4, decanted and concentrated to a yellow oil which was used in the next step without further purification.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. additionThe reaction was diluted with 50 mL of saturated bicarbarbonate
  4. customthe layers were separated
  5. washThe organic layer was washed once more with 50 mL of sodium bicarbonate
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated to a yellow oil which
  9. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-80da9c884ca942a2b874fa572c3be14d
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

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