Morpholine → 4-(4-Nitro-phenyl)-1-piperidin-1-yl-butan-1-one

HRID 1884479Notes

Reaction equation

HRID 1884479 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:16]1[CH2:21][CH2:20]O[CH2:18][CH2:17]1.[C:22](=O)(O)[O-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]([N:16]2[CH2:21][CH2:20][CH2:22][CH2:18][CH2:17]2)=[O:15])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 797114-(4-Nitrophenyl)butyric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 219749904-(4-Nitro-phenyl)-1-piperidin-1-yl-butan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A room temperature solution of 1.1220 gms. 4-(4-nitro-phenyl)-butyric acid in tetrahydrofuran (3 mL) is treated with 0.8978 gms. 1′,1′-carbonyl-diimidizole using an ice bath to attenuate the intensity of the reaction. The reaction mixture is stirred for 30 minutes in the ice bath and 30 minutes at room temperature. The reaction mixture is then treated with 0.5 mL morpholine. The reaction was heated overnight at 35° C. The reaction is then allowed to cool to room temperature, and is made basic with the addition of saturated aqueous sodium bicarbonate. The resulting mixture is extracted with ethyl acetate. The organics are dried over anhydrous sodium sulfate, filtered and evaporated to dryness in vacuo. The crude product residue is then purified by filtering it through a plug of silica gel using 50% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 4-(4-nitro-phenyl)-1-piperidin-1-yl-butan-1-one is isolated as a yellow oil in the amount of 1.47 gms.

Workup

  1. customA room temperature solution of 1.1220 gms
  2. customthe intensity of the reaction
  3. temperatureto cool to room temperature
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. dry with materialThe organics are dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe crude product residue is then purified
  9. filtrationby filtering it through a plug of silica gel using 50% ethyl acetate in hexanes as the eluant
  10. customevaporation of solvent

Sources & evidence

ORD record
ord-55547bf04c184b23aeaaab6cf1380698
Source dataset
uspto-grants-2004_07
Patent number
US06765012B2

Reaction notes

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