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

HRID 908919Notes

Reaction equation

HRID 908919 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.[CH3:23][N:24]1[CH2:29]CO[CH2:26][CH2:25]1.Cl.CN(C)[C:33]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)CC[C:36](=[CH:39][C:40](O)=[O:41])[CH2:35][CH2:34]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:29][N:24]([CH:25]1[CH2:26][CH:33]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:34][CH2:35][C:36]1=[CH:39][C:40]([NH: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)=[O:41])[CH3:23]

Participants

9

Reactant 6

HCID 1150TryptamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386703(4-Dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride

Product 1

HCID 673864932-(Dimethylamino-4-phenylcyclohexylidene)-N-[2-(1H-indol-3-yl)ethyl]acetamideYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (182 mg, 1.35 mmol), tryptamine (108 mg, 0.676 mmol) and N-methylmorpholine (0.148 ml, 1.35 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexylidene)acetic acid hydrochloride (200 mg, 0.676 mmol) in dry dimethylformamide (10 ml) under argon. The clear solution was cooled to 0° C. and dicyclohexylcarbodiimide (278 mg, 1.35 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 (150 ml). The product thereby precipitated out as a colourless solid in a yield of 31% (84 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. customThe filtrate obtained
  8. extractionwas extracted with ether
  9. customThe product thereby precipitated out as a colourless solid in a yield of 31% (84 mg)

Sources & evidence

ORD record
ord-6e76dea21b6e4d438f67f4cda060ca2c
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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