Triethylamine → HCID 44212570, compound

HRID 1075537Notes

Reaction equation

HRID 1075537 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=1[N:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.C(N(CC)CC)C>S(Cl)(Cl)=O.ClCCl>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:16][C:15]=1[N:21]1[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 74654Benzeneacetic acid, 4-bromo-HCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 44212570HCID 44212570, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

4Bromophenylacetic acid (0.300 g, 1.40 mmol) was suspended in thionyl chloride (10 ml) and heated to reflux with stirring. After 1 h, the reaction mixture was allowed to cool and was evaporated under reduced pressure to give a yellow oil. The oil was then azeotroped with toluene, and the residue dried in vacuo to give the crude acid chloride. Meanwhile 4-methoxy-3-(4-methyl-1-piperazinyl)benzeneamine (EP 0533 267 A1) (0.293 g, 1.33 mmol) was dissolved in dichloromethane (10 ml) and treated with triethylamine (0.195 ml, 1.40 mmol), followed by dropwise addition of a solution of the crude acid chloride in dichloromethane (3 ml). The mixture was stirred at room temperature overnight before being washed with NaHCO3 solution. The organic layer was then dried (Na2SO4), and was evaporated under reduced pressure to give a brown oil. The oil was purified by silica-gel chromatography (5% MeOH/CH2Cl2 as eluant) to give the title compound as a pale yellow oil (0.295 g, 50%), which was converted to its oxalate salt.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureto cool
  4. customwas evaporated under reduced pressure
  5. customto give a yellow oil
  6. customThe oil was then azeotroped with toluene
  7. customthe residue dried in vacuo
  8. customto give the crude acid chloride
  9. stirringThe mixture was stirred at room temperature overnight
  10. washbefore being washed with NaHCO3 solution
  11. dry with materialThe organic layer was then dried (Na2SO4)
  12. customwas evaporated under reduced pressure
  13. customto give a brown oil
  14. customThe oil was purified by silica-gel chromatography (5% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-0b9344d77c3243f1906aea9016da4edc
Source dataset
uspto-grants-1999_05
Patent number
US05905080

Reaction notes

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