Cyclohexylamine → 4-Bromo-N-cyclohexyl-2-fluorobenzamide

HRID 911293Notes

Reaction equation

HRID 911293 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:11])[CH:3]=1.C(N(CC)CC)C.[CH:19]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:25][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 27340264-Bromo-2-fluorobenzoyl chloride

Product 1

HCID 90711954-Bromo-N-cyclohexyl-2-fluorobenzamideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 4-bromo-2-fluoro-benzoyl chloride (1 g, 4.21 mmol) in DCM and cool the solution in an ice bath. Add triethylamine (0.87 mL, 6.32 mmol) and cyclohexylamine (502 mg, 5.1 mmol) and stir the mixture at ambient temperature for 2 h. Partition the reaction mixture between brine and DCM. Dry the organic layer over Na2SO4, filter and concentrate in vacuo to give the desired intermediate as a white solid (1.24 g, 98%).

Workup

  1. temperaturecool the solution in an ice bath
  2. customPartition the reaction mixture between brine and DCM
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-7239490edb344e0b8f836e1eae6e75fb
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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