4-Methylmorpholine → 2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[3-(1H-indol-3-yl)propyl]acetamide

HRID 908937

Reaction equation

HRID 908937 reaction equation
ON1C2C=CC=CC=2N=N1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][CH2:21][CH2:22][NH2:23])=[CH:12]1.CN1CCOCC1.Cl.[CH3:32][N:33]([CH3:50])[C:34]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:39][CH2:38][C:37](=[CH:40][C:41](O)=[O:42])[CH2:36][CH2:35]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:50][N:33]([CH3:32])[C:34]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:39][CH2:38][C:37](=[CH:40][C:41]([NH:23][CH2:22][CH2:21][CH2:20][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][CH:12]=2)=[O:42])[CH2:36][CH2:35]1

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 289891H-indole-3-propylamineHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

Product 1

HCID 116553572-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[3-(1H-indol-3-yl)propyl]acetamideYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (819 mg, 6.0 mmol), 3-(1H-indol-3-yl)propylamine (522 mg, 3.0 mmol) and N-methylmorpholine (0.666 ml, 6.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (887 mg, 3.0 mmol) in dry dimethylformamide (10 ml) under argon. The solution was cooled to 0° C. and dicyclohexylcarbodiimide (1.25 g, 6.0 mmol) was added. The reaction mixture was stirred at RT for 6 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 aqueous phase was diluted with water (400 ml), 5 M sodium hydroxide solution (5 ml, 25 mmol) was added and the mixture was stored at 5° C. for 3 d. The product thereby precipitated out as a beige-coloured solid in a yield of 60% (742 mg) with an m.p. of 85-87° 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. additionwas added
  8. waitthe mixture was stored at 5° C. for 3 d
  9. customThe product thereby precipitated out as a beige-coloured solid in a yield of 60% (742 mg) with an m.p. of 85-87° C.

Sources & evidence

ORD record
ord-abc4871d7af74b08804964c15cf9de0e
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Linked notes

Loading…