Potassium Carbonate → 1-(3,4,5-Trimethoxyphenyl)piperazine

HRID 1533893Notes

Reaction equation

HRID 1533893 reaction equation
Cl.Cl[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[NH2:14].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:21][O:20][C:16]1[CH:15]=[C:13]([N:14]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)[CH:12]=[C:11]([O:10][CH3:9])[C:17]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 322853,4,5-TrimethoxyanilineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 38387651-(3,4,5-Trimethoxyphenyl)piperazineYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 44.3 g (0.25 mol) of bis(2-chloroethyl)amine hydrochloride and 45.5 g (0.25 mol) of 3,4,5-trimethoxyaniline in 550 mL of absolute ethanol was heated at reflux for 16 h under a nitrogen atmosphere. The mixture was cooled and 50.0 g (0.36 mol) of potassium carbonate was added and heating was continued for 16 h. The hot mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was triturated with ethyl acetate. The collected solid was re-crystallized from 2-propanol/methanol. The solid was dissolved in 5.9N sodium hydroxide and the solution was continuously extracted with chloroform for 5 h. The organic layer was dried (MgSO4), concentrated under reduced pressure, and the residue was triturated with cyclohexane/petroleum ether (30°-60°) to give 23.6 g (38%) of white solid, mp 73°-77° C.

Workup

  1. temperatureat reflux for 16 h under a nitrogen atmosphere
  2. temperatureThe mixture was cooled
  3. temperatureheating
  4. filtrationThe hot mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was triturated with ethyl acetate
  7. customThe collected solid was re-crystallized from 2-propanol/methanol
  8. dissolutionThe solid was dissolved in 5.9N sodium hydroxide
  9. extractionthe solution was continuously extracted with chloroform for 5 h
  10. dry with materialThe organic layer was dried (MgSO4)
  11. concentrationconcentrated under reduced pressure
  12. customthe residue was triturated with cyclohexane/petroleum ether (30°-60°)

Sources & evidence

ORD record
ord-13da3cd138974f898403895d772e1a3c
Source dataset
uspto-grants-1992_02
Patent number
US05086055

Reaction notes

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