Morpholine → HCID 21975163, compound

HRID 1884478Notes

Reaction equation

HRID 1884478 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:19][CH2:18][CH2:17]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[N:16]1([C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

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

Product 1

HCID 21975163HCID 21975163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A room temperature solution of 1.1180 gms. 4-(4-nitro-phenyl)-butyric acid in tetrahydrofuran (3 mL) is treated with 0.9052 gms. 1′,1′-carbonyl-diimidizole using an ice bath to attenuate the intensity of the reaction. The reaction mixture is stirred for 1 h. The reaction mixture is then treated with 0.5 mL morpholine. The reaction is 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 chromatographed by flash silica gel chromatography using 60% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 1-morpholin-4-yl-4-(4-nitro-phenyl)-butan-1-one is isolated as a white solid in the amount of 1.3925 gms.

Workup

  1. customA room temperature solution of 1.1180 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 chromatographed by flash silica gel chromatography
  9. customevaporation of solvent

Sources & evidence

ORD record
ord-e678d879f78b441ca5ae18ce2c54bb49
Source dataset
uspto-grants-2004_07
Patent number
US06765012B2

Reaction notes

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