Water → (3-Methyl-4-nitrophenyl)-(4-methylpiperazin-1-yl)methanone

HRID 1260367Notes

Reaction equation

HRID 1260367 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.O>ClCCCl>[CH3:1][C:2]1[CH:3]=[C:4]([C:5]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)=[O:7])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 183703-Methyl-4-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 531671-Methylpiperazine

Product 1

HCID 718014(3-Methyl-4-nitrophenyl)-(4-methylpiperazin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

3-Methyl-4-nitrobenzoic acid (5.525 mmol, 1.0 gram) was taken in a 25 mL two necked round bottom flask attached with a condenser, provided with a guard tube. To this, thionyl chloride (6.07 mmol, 0.735 gram) and 1,2-dichloroethane (5 mL) were added and the solution was refluxed for a period of 3 hours. This reaction mixture was added to another 100 mL flask, containing a solution of N-methylpiperazine (16.57 mmol, 1.66 grams) in 10 mL 1,2-dichloroethane, which is maintained at temperature below 5° C. The reaction mixture was then stirred for 0.5 hour at 25° C. After the completion of reaction, the reaction mixture was poured onto 50 mL water. 1,2-dichloroethane layer was separated, washed with water (2×10 mL), brine (10 mL) and dried over anhydrous sodium sulfate. The volatiles were removed under the reduced pressure to obtain thick syrupy mass. This thick syrupy mass was used for next step of reaction without purification.

Workup

  1. customattached with a condenser
  2. customprovided with a guard tube
  3. temperaturethe solution was refluxed for a period of 3 hours
  4. additionThis reaction mixture was added to another 100 mL flask
  5. temperatureis maintained at temperature below 5° C
  6. customAfter the completion of reaction
  7. custom1,2-dichloroethane layer was separated
  8. washwashed with water (2×10 mL), brine (10 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe volatiles were removed under the reduced pressure
  11. customto obtain thick syrupy mass
  12. customThis thick syrupy mass was used for next step of reaction without purification

Sources & evidence

ORD record
ord-f585acf8bc0941c2bf779c0aef9db7f4
Source dataset
uspto-grants-2013_06
Patent number
US08470830B2

Reaction notes

Loading…