4-Methylmorpholine → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(4-fluoro-phenyl)acetamide

HRID 908930

Reaction equation

HRID 908930 reaction equation
ON1C2C=CC=CC=2N=N1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.CN1CCOCC1.Cl.[CH3:27][N:28]([CH3:45])[C:29]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:34][CH2:33][C:32](=[CH:35][C:36](O)=[O:37])[CH2:31][CH2:30]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:45][N:28]([CH3:27])[C:29]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:34][CH2:33][C:32](=[CH:35][C:36]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([F:11])=[CH:13][CH:14]=2)=[O:37])[CH2:31][CH2:30]1

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 97314-FluoroanilineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

Product 1

HCID 115383312-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(4-fluoro-phenyl)acetamideYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (273 mg, 2.0 mmol), 4-fluoroaniline (0.095 ml, 1.0 mmol) and N-methylmorpholine (0.222 ml, 2.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (296 mg, 1.0 mmol) in dry dimethylformamide (10 ml) under argon. The solution was cooled to 0° C. and dicyclohexylcarbodiimide (417 mg, 2.0 mmol) was added. The reaction mixture was stirred at RT for 7 d. Working up of the mixture was carried out by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). Still further urea thereby precipitated out and was separated off. 5 M sodium hydroxide solution (4 ml, 20 mmol) was added to the aqueous phase and the mixture was diluted with water (300 ml) and stored at 5° C. for 3 d. The product thereby precipitated out as a colourless solid in a yield of 82% (287 mg).

Workup

  1. customby separating off the urea which
  2. customhad precipitated out
  3. additionintroducing the filtrate
  4. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  5. customStill further urea thereby precipitated out and
  6. customwas separated off
  7. waitstored at 5° C. for 3 d
  8. customThe product thereby precipitated out as a colourless solid in a yield of 82% (287 mg)

Sources & evidence

ORD record
ord-829042f2a02e4e5a8c922df054972f75
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Linked notes

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