Benzylamine → N-Benzyl-2-(4-dimethylamino-4-phenylcyclohexylidene)-acetamide

HRID 908928

Reaction equation

HRID 908928 reaction equation
ON1C2C=CC=CC=2N=N1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[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>[CH2:11]([NH:18][C:36](=[O:37])[CH:35]=[C:32]1[CH2:31][CH2:30][C:29]([N:28]([CH3:45])[CH3:27])([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:34][CH2:33]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 6

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

Product 1

HCID 11660991N-Benzyl-2-(4-dimethylamino-4-phenylcyclohexylidene)-acetamideYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (273 mg, 2.0 mmol), benzylamine (0.109 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 12 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 65% (227 mg) and with an m.p. of 145-148° 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. waitstored at 5° C. for 3 d
  8. customThe product thereby precipitated out as a colourless solid in a yield of 65% (227 mg) and with an m.p. of 145-148° C.

Sources & evidence

ORD record
ord-2ff0f76859ab4e999daeeb6d5a50e577
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Linked notes

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