Hydrochloric Acid → Hydrochloric Acid

HRID 1995911Notes

Reaction equation

HRID 1995911 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][CH2:15][CH2:16]Br)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[NH2:18][CH2:19][CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:36]>CN(C)C=O.O.C(O)C>[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][CH2:15][CH2:16][NH:18][CH2:19][CH2:20][C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].[ClH:36]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1150TryptamineHCID 11430Potassium CarbonateHCID 900187-(3-Bromopropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione

Product 2

HCID 313Hydrochloric AcidHCID 13023328N-[3-(Theophyllin-7-yl)propyl]tryptamine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 3-(theophyllin-7-yl)propyl bromide (3.0 g., 0.01 mole), tryptamine base (1.60; 0.01 mole) and potassium carbonate (4 g; 0.029 mole) in dry dimethylformamide (50 cc.) was heated, under a dry nitrogen blanket, in an oil-bath maintained at 75° for 17.5 hours. After cooling, the dark mixture was diluted with water (200 cc.) and extracted with dichloromethane (2×50 cc.). The combined extracts were washed with water (2×100 cc.) and dried (MgSO4). Filtration and evaporation gave a syrup which was dissolved in a little ethanol and acidified with ethanolic hydrogen chloride. After cooling, the precipitated crystals were filtered off and washed well with ethanol and ethyl acetate to give the title compound hydrochloride, m.p. 273°-274° C. (dec.) (partial decomposition above 265° C.). The product may also be designated as 3,7-dihydro-7-[3-[[2-(1H-indol-3-yl)ethyl]amino]propyl]-1,3-dimethyl-1H-purine-2,6-dione,hydrochloride. The yield was 1.99 g.

Workup

  1. temperaturewas heated, under a dry nitrogen blanket
  2. temperaturein an oil-bath maintained at 75° for 17.5 hours
  3. temperatureAfter cooling
  4. extractionextracted with dichloromethane (2×50 cc.)
  5. washThe combined extracts were washed with water (2×100 cc.)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation
  8. customgave a syrup which
  9. temperatureAfter cooling
  10. filtrationthe precipitated crystals were filtered off
  11. washwashed well with ethanol and ethyl acetate

Sources & evidence

ORD record
ord-7cf10f924c714ea6be9793a1d6de94a1
Source dataset
uspto-grants-1983_09
Patent number
US04406903

Reaction notes

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