4-Nitrobenzoic Acid → 1-(4-Nitrobenzoyl)piperidine

HRID 2219148Notes

Reaction equation

HRID 2219148 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[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:10])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 8082PiperidineHCID 516892Sodium Bicarbonate

Product 1

HCID 2254681-(4-Nitrobenzoyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A room temperature solution of 5.04 gms. 4-nitro-benzoic acid in tetrahydrofuran (10 mL) is treated with 5.14 gms. 1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath. The reaction mixture is stirred in the ice bath for 30 minutes, then it is allowed to warm to room temperature. Once at room temperature the reaction mixture is treated with 3 mL piperidine. The reaction mixture is allowed to stir at room temperature overnight. The reaction is then made basic with the addition of saturated aqueous sodium bicarbonate solution, and the resulting mixture is extracted with ethyl acetate. The organics are separated, dried over anhydrous sodium sulfate, and subsequently evaporated to dryness in vacuo. The crude product residue is then chromatographed by flash silica gel chromatography using 50% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 1-(4-nitrobenzoyl)piperidine is isolated as a white solid in the amount of 5.87 gms.

Workup

  1. customA room temperature solution of 5.04 gms
  2. custom1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. customThe organics are separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customsubsequently evaporated to dryness in vacuo
  7. customThe crude product residue is then chromatographed by flash silica gel chromatography
  8. customevaporation of solvent

Sources & evidence

ORD record
ord-9a23f3cd5e834ea18a189f81e60c5850
Source dataset
uspto-grants-2008_08
Patent number
US07414054B2

Reaction notes

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