4-Nitrobenzoic Acid → (4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone

HRID 871842Notes

Reaction equation

HRID 871842 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>CN(C=O)C.ClCCl.[Na+].[Cl-]>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:8]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)=[O:10])[CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 531671-MethylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 716396(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanoneYield 56%

Reagents, catalysts & solvents 3

HCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
3.5 °C

Procedure

A mixture of 2.0 g of 4-nitrobenzoic acid (11.97 mmol), 10.42 mL of diisopropylethylamine (59.84 mmol) and 1.46 mL of 1-methylpiperazine (13.16 mmol) in 40 mL of DMF is cooled to 2-5°C. on an ice bath. 11.53 g (35.9 mmol) of O-benzotriazolyltetramethylisouronium tetrafluoroborate (TBTU, CAS No.=125700-67-6) are then added portionwise and the mixture is stirred at temperature overnight. The reaction mixture is diluted with dichloromethane and saturated aqueous NaCl solution. After separation of the phases by settling, the aqueous phase is extracted with dichloromethane. The organic phases are combined, dried over Na2SO4, filtered and concentrated under vacuum. The oily residue containing insoluble material is drained by suction and then rinsed with dichloromethane and a small amount of methanol. 1.67 g of the expected product are obtained in the form of a pale pink solid, which is used as obtained without further purification. Yield=56%.

Workup

  1. customAfter separation of the phases
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. additionThe oily residue containing insoluble material
  7. washrinsed with dichloromethane

Sources & evidence

ORD record
ord-6fca42a174844a2a9eb785e04712cd97
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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