Piperazine → HCID 22326795, compound

HRID 495490Notes

Reaction equation

HRID 495490 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([O:14][CH3:15])[C:6]=1[O:16][CH3:17].C([O-])([O-])=O.[K+].[K+].[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.N1CCNCC1>CC#N>[CH3:17][O:16][C:6]1[C:7]([O:14][CH3:15])=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][N:28]1[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 11430Potassium Carbonate2×HCID 531671-MethylpiperazineHCID 22326834HCID 22326834, compound

Product 1

HCID 22326795HCID 22326795, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-chloroethoxy)-2,3-dimethoxy-5-nitrobenzene (1.382 g, 5.28 mmol), K2CO3 (1.83 g, 13.2 mmol), and N-methylpiperazine (1.76 mL, 15.85 mmol) was stirred and heated under N2 in CH3CN (20 mL) under reflux overnight. The next day 0.80 g K2CO3 and 0.66 mL piperazine were added (1.1 eq.) and heated for 3 h more when HPLC showed that the reaction was complete. The solids were filtered and washed well with CH3CN and the filtrate was evaporated at 80° C. to remove excess amine. The resulting red oil was dissolved in CH2Cl2 and washed with water. The aqueous layer was washed with CH2Cl2. The combined organic layers were dried and evaporated giving 2,3-dimethoxy-1-(2-(4-methylpiperazin-1-yl)ethoxy)-5-nitrobenzene.

Workup

  1. temperatureunder reflux overnight
  2. temperatureheated for 3 h more when HPLC
  3. filtrationThe solids were filtered
  4. washwashed well with CH3CN
  5. customthe filtrate was evaporated at 80° C.
  6. customto remove excess amine
  7. dissolutionThe resulting red oil was dissolved in CH2Cl2
  8. washwashed with water
  9. washThe aqueous layer was washed with CH2Cl2
  10. customThe combined organic layers were dried
  11. customevaporated

Sources & evidence

ORD record
ord-6f6b830d5b124ba48cf853e7d664df0f
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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