Tryptamine → 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexylidene]-N-[2-(1H-indol-3-yl)ethyl]acetamide

HRID 908947Notes

Reaction equation

HRID 908947 reaction equation
ON1C2C=CC=CC=2N=N1.[NH2:11][CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.CN1CCOCC1.Cl.[CH3:31][N:32]([CH3:50])[C:33]1([C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[CH2:38][CH2:37][C:36](=[CH:39][C:40](O)=[O:41])[CH2:35][CH2:34]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>O.CN(C)C=O>[CH3:50][N:32]([CH3:31])[C:33]1([C:43]2[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=2)[CH2:38][CH2:37][C:36](=[CH:39][C:40]([NH:11][CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:41])[CH2:35][CH2:34]1

Participants

9

Reactant 6

HCID 1150TryptamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386287HCID 67386287, compound

Product 1

HCID 117051782-[4-dimethylamino-4-(4-fluorophenyl)cyclohexylidene]-N-[2-(1H-indol-3-yl)ethyl]acetamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (864 mg, 6.4 mmol), tryptamine (512 mg, 3.2 mmol) and N-methylmorpholine (0.703 ml, 6.4 mmol) were added to a solution of (4-dimethylamino-4-(4-fluorophenyl)cyclohexylidene)acetic acid hydrochloride (840 mg, 3.2 mmol) in abs. dimethylformamide (25 ml) under argon. The solution was cooled to 0° C., dicyclohexylcarbodiimide (1.32 g, 6.4 mmol) was added and the mixture was stirred at RT for 4 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 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 4 d. The product thereby precipitated out as a beige-coloured oily solid in a yield of 95% (1.27 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. additionwas added
  8. waitthe mixture was stored at 5° C. for 4 d
  9. customThe product thereby precipitated out as a beige-coloured oily solid in a yield of 95% (1.27 mg)

Sources & evidence

ORD record
ord-dbf86c35b6574955bf25d73aa75aa925
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

Loading…