4-Methylmorpholine → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(3-phenyl-propyl)acetamide

HRID 908924Notes

Reaction equation

HRID 908924 reaction equation
ON1C2C=CC=CC=2N=N1.[C:11]1([CH2:17][CH2:18][CH2:19][NH2:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN1CCOCC1.Cl.[CH3:29][N:30]([CH3:47])[C:31]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:36][CH2:35][C:34](=[CH:37][C:38](O)=[O:39])[CH2:33][CH2:32]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:47][N:30]([CH3:29])[C:31]1([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:36][CH2:35][C:34](=[CH:37][C:38]([NH:20][CH2:19][CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:39])[CH2:33][CH2:32]1

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 162593-PhenylpropylamineHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

Product 1

HCID 115171962-(4-Dimethylamino-4-phenylcyclohexylidene)-N-(3-phenyl-propyl)acetamideYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (273 mg, 2.0 mmol), 3-phenyl-1-propylamine (0.142 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 (300 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 3 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. The filtrate obtained was extracted with ether. 5 M sodium hydroxide solution (2 ml, 10 mmol) was added to the aqueous phase and the mixture was diluted with water (200 ml). The product thereby precipitated out as a colourless solid and was to be obtained in a yield of 55% (209 mg) with an m.p. of 140-142° C.

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. customThe filtrate obtained
  8. extractionwas extracted with ether
  9. customThe product thereby precipitated out as a colourless solid
  10. customto be obtained in a yield of 55% (209 mg) with an m.p. of 140-142° C.

Sources & evidence

ORD record
ord-b69edffb620b450fad31820f950a74d9
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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