Pyridine → (4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone

HRID 2410704Notes

Reaction equation

HRID 2410704 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C1COCC1>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 531671-Methylpiperazine

Product 1

HCID 716396(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanoneYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 1-liter-3-neck flask was loaded with 4-nitrobenzoyl chloride (50.5 g, 267 mmol) and THF (500 ml) and cooled to 0° C. Pyridine (44 ml, 544 mmol), then 1-methyl-piperazine (35 ml, 316 mmol) were added while mechanically stirring at 0° C. After the addition was completed the ice bath was removed and the mixture stirred for 1 hour, while warming to room temperature. A voluminous precipitate forms. The slurry was diluted with dichloromethane and 1 M aq. KOH and the layers separated. The organic layer was washed one more time with 1 M aq. KOH, then with brine and dried over MgSO4, filtered and concentrated in vacuum. 31.5 g yellow solid (4-methylpiperazin-1-yl)(4-nitrophenyl)methanone were isolated. MS (ESI) m/z 250 (M+H). 1H NMR (CDCl3) δ ppm 8.27 (d, 2H, J=7.9), 7.56 (d, 2H, J=7.9), 3.81 (bs, 2H), 3.37 (bs, 2H), 2.50 (bs, 2H), 2.34 (bs, 2H), 2.32 (s, 3H).

Workup

  1. additionAfter the addition
  2. customwas removed
  3. stirringthe mixture stirred for 1 hour
  4. temperaturewhile warming to room temperature
  5. additionThe slurry was diluted with dichloromethane and 1 M aq. KOH
  6. customthe layers separated
  7. washThe organic layer was washed one more time with 1 M aq. KOH
  8. dry with materialwith brine and dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-faec7969d27442f59c5d980cfc76e768
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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