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

HRID 908954Notes

Reaction equation

HRID 908954 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.[CH3:30][N:31]([CH3:49])[C:32]1([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=2)[CH2:37][CH2:36][C:35](=[CH:38][C:39](O)=[O:40])[CH2:34][CH2:33]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:49][N:31]([CH3:30])[C:32]1([C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[CH:43]=2)[CH2:37][CH2:36][C:35](=[CH:38][C:39]([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:40])[CH2:34][CH2:33]1

Participants

9

Reactant 6

HCID 1150TryptamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386283[4-Dimethylamino-4-(3-fluoro-phenyl)-cyclohexylidene]acetic acid

Product 1

HCID 115470202-[4-dimethylamino-4-(3-fluorophenyl)cyclohexylidene]-N-[2-(1H-indol-3-yl)ethyl]acetamideYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (1.08 g, 8.0 mmol), tryptamine (640 mg, 4.0 mmol) and N-methylmorpholine (0.888 ml, 8.0 mmol) were added to a solution of [4-dimethylamino-4-(3-fluoro-phenyl)-cyclohexylidene]acetic acid (1.55 g, 4.0 mmol) in dry dimethylformamide (15 ml) under argon. The solution was cooled to 0° C., dicyclohexylcarbodiimide (1.64 g, 8.0 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 aqueous phase was diluted with water (300 ml), 5 M sodium hydroxide solution (7 ml, 35 mmol) was added and the mixture was stored at 5° C. for 16 h. The crude product thereby precipitated out as a beige-coloured solid (1.3 g). After chromatography on silica gel (60 g) with EA/methanol (6:1), the product was obtained in a yield of 62% (1.03 g) with an m.p. of 172-176° 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 16 h
  9. customThe crude product thereby precipitated out as a beige-coloured solid (1.3 g)
  10. customAfter chromatography on silica gel (60 g) with EA/methanol (6:1), the product was obtained in a yield of 62% (1.03 g) with an m.p. of 172-176° C.

Sources & evidence

ORD record
ord-3bc3115617f14f1aa9b03257faeb2790
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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