Tryptamine → HCID 11662172, compound

HRID 908983Notes

Reaction equation

HRID 908983 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]([CH3:48])[C:32]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[CH2:37][CH2:36][CH:35]([CH2:38][C:39](O)=[O:40])[CH2:34][CH2:33]1.C1(N=C=NC2CCCCC2)CCCCC1.C(NC1CCCCC1)(NC1CCCCC1)=O.[OH-].[Na+]>O.CN(C)C=O>[CH3:48][N:31]([CH3:30])[C:32]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[CH2:33][CH2:34][CH:35]([CH2:38][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])[CH2:36][CH2:37]1

Participants

10

Reactant 7

HCID 1150TryptamineHCID 4277N,N'-DicyclohexylureaHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386533HCID 67386533, compound

Product 1

HCID 11662172HCID 11662172, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (432 mg, 3.2 mmol), tryptamine (256 mg, 1.6 mmol) and N-methylmorpholine (0.352 ml, 3.2 mmol) were added to a solution of the more polar diastereoisomer of (4-dimethylamino-4-pyridin-2-yl-cyclohexyl)-acetic acid (476 mg, 1.6 mmol) in abs. dimethylformamide (20 ml) under argon. The solution was cooled in an ice-bath, dicyclohexylcarbodiimide (660 mg, 3.2 mmol) was added and the mixture was stirred at RT for 13 d, during which dicyclohexylurea precipitated out. 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 oily compound (319 mg, 49%). After purification by chromatography on silica gel (45 g) with methanol and methanol/30 percent strength aqueous ammonia (100:1), the product was obtained as a beige-coloured oil in a yield of 12% (80 mg).

Workup

  1. temperatureThe solution was cooled in an ice-bath
  2. customprecipitated out
  3. customby separating off the urea which
  4. customhad precipitated out
  5. additionintroducing the filtrate
  6. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  7. customStill further urea thereby precipitated out and
  8. customwas separated off
  9. additionwas added
  10. customThe crude product thereby precipitated out as a beige-coloured oily compound (319 mg, 49%)
  11. customAfter purification by chromatography on silica gel (45 g) with methanol and methanol/30 percent strength aqueous ammonia (100:1)
  12. customthe product was obtained as a beige-coloured oil in a yield of 12% (80 mg)

Sources & evidence

ORD record
ord-20e2894259034e499f5eae71f9e436d0
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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