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

HRID 888567

Reaction equation

HRID 888567 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.C1C=CC2C=[C:25]([NH2:30])C=CC=2C=1.Cl.CN(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:30][CH3:25])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70572-NaphthylamineHCID 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 napthylamine (40% solution in water, 0.11 μl, 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-f1a9e204f11d4b1ca2f4c7bf63151e25
Source dataset
uspto-grants-2012_08
Patent number
US08247576B2

Linked notes

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