(4-Nitrophenyl)acetic acid → 1-[(4-Nitrophenyl)acetyl]piperidine

HRID 11552

Reaction equation

HRID 11552 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8082PiperidineHCID 516892Sodium Bicarbonate

Product 1

HCID 35942761-[(4-Nitrophenyl)acetyl]piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A room temperature solution of 2.53 gms. (4-Nitro-phenyl)-acetic acid in tetrahydrofuran (10 mL) is treated with 2.44 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 1.21 mL piperidine, and then is stirred overnight at room temperature. The reaction is then made basic with the addition of saturated aqueous sodium bicarbonate, and the resulting mixture is extracted with ethyl acetate. The organics are separated, dried over anhydrous sodium sulfate, filtered, 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, 2-(4-nitro-phenyl)-1-piperidin-1-yl-ethanone is isolated as a white solid in the amount of 3.18 gms.

Workup

  1. customA room temperature solution of 2.53 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. filtrationfiltered
  7. customsubsequently evaporated to dryness in vacuo
  8. customThe crude product residue is then chromatographed by flash silica gel chromatography
  9. customevaporation of solvent

Sources & evidence

ORD record
ord-05ec8b81a6074b43aabbd230172ff7a9
Source dataset
uspto-grants-2006_08
Patent number
US07098236B2

Linked notes

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