4-Nitrobenzoic Acid → (4-Nitrophenyl)(pyrrolidin-1-yl)methanone

HRID 546616Notes

Reaction equation

HRID 546616 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].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.OC1C2N=NNC=2C=CC=1.CNC(N=C=NCC)CCNC.C(NC(C)C)(C)C>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:10])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 61084-Nitrobenzoic AcidHCID 7912DiisopropylamineHCID 31268PyrrolidineHCID 230638731,3-Dimethylaminopropyl-3-ethylcarbodiimideHCID 178418300HCID 178418300, compound

Product 1

HCID 386112(4-Nitrophenyl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.98 g of para-nitrobenzoic acid in 50 mL of dichloromethane are successively added under argon, at 0° C., 0.781 mL of pyrrolidine, 0.13 g of hydroxybenzotriazole, 2.3 g of 1,3-dimethylaminopropyl-3-ethyl carbodiimide and 3.43 mL of diisopropylamine. The reaction mixture is then stirred at room temperature for 15 hours and then washed with water. The organic phase is then washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of ethyl acetate and cyclohexane (60/40 by volume) to give 1.9 g of (4-nitrophenyl)pyrrolidin-1-yl-methanone, the characteristics of which are as follows:

Workup

  1. washwashed with water
  2. washThe organic phase is then washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography on a column of silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane (60/40 by volume)

Sources & evidence

ORD record
ord-f04cb732e13d4d9ea69cd08d4fa3d1b7
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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