Methylamine → 3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide

HRID 45489Notes

Reaction equation

HRID 45489 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.CN.Cl.[CH3:23][N:24](C)CCCC(N=C=N)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][C:10]([NH:24][CH3:23])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 219829211-(3-Dimethylaminopropyl)ethylcarbodiimide hydrochlorideHCID 576913963-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid

Product 1

HCID 593319703-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-N-methyl-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid (0.25 g, 0.74 mmol) and 1-hydroxybenatriazole (0.12 g, 0.88 mmol) in dichloromethane (3 ml) was stirred for 15 minutes before addition of methylamine (40% solution in water, 0.110, 1.47 mmol) and 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (0.17 g, 0.88 mmol). The reaction mixture was stirred for 16 hours, solvent removed under reduced pressure and the residue partitioned between ethyl acetate and 1N HCl. The organic layer was separated, washed with saturated sodium hydrogen carbonate, brine, dried (MgSO4), filtered and concentrated to yield the title compound which was used in the next step without further purification. LC/MS: (PS-A2) Rt 3.20 [M+H]+ 353.95.

Workup

  1. customsolvent removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and 1N HCl
  3. customThe organic layer was separated
  4. washwashed with saturated sodium hydrogen carbonate, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bcb8c9e4374648ec93c815f1d0e4a343
Source dataset
uspto-grants-2013_09
Patent number
US08541461B2

Reaction notes

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