Triethylamine → HCID 13491625, compound

HRID 1284916Notes

Reaction equation

HRID 1284916 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].C(N(CC)CC)C.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23]>C(O)C>[CH3:1][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11])[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 409438N-Methyl-1-(2-nitrophenyl)methanamine

Product 1

HCID 13491625HCID 13491625, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

135.8 g (0.67 mol) of methyl-(2-nitrobenzyl)-amine and 187.5 ml (1.339 mols) of triethylamine are dissolved in 1.87 liters of ethanol at room temperature, with stirring, and 148 g (0.682 mol) of 2-bromo-1-(4-fluorophenyl)ethanone are then added in portions. The reaction mixture is stirred for 3 hours. The solvent is then stripped off on a rotary evaporator and the residue is dissolved in 1.3 liters of toluene. The toluene phase is washed several times with H2O and dried over Na2SO4, and HCl/diethyl ether is added. The glutinous precipitate is separated from the toluene by decanting and crystallized with acetone. The colorless precipitate is filtered off with suction and dried.

Workup

  1. stirringThe reaction mixture is stirred for 3 hours
  2. customThe solvent is then stripped off on a rotary evaporator
  3. dissolutionthe residue is dissolved in 1.3 liters of toluene
  4. washThe toluene phase is washed several times with H2O
  5. dry with materialdried over Na2SO4, and HCl/diethyl ether
  6. additionis added
  7. customThe glutinous precipitate is separated from the toluene
  8. customby decanting
  9. customcrystallized with acetone
  10. filtrationThe colorless precipitate is filtered off with suction
  11. customdried

Sources & evidence

ORD record
ord-01c525570d0e42d39fe46ed2d590b5db
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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