Sodium Chloride → 2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate

HRID 264549Notes

Reaction equation

HRID 264549 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][N:13]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[C:14]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-:21].[K+].[Cl-].[Na+].[CH2:25]([OH:28])[CH2:26]O.[OH2:29]>>[C:18]([OH:20])(=[O:29])/[CH:19]=[CH:26]/[C:25]([OH:28])=[O:21].[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][N:13]([CH2:15][CH2:16][NH2:17])[C:14]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036432HCID 19036432, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 190364442-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarateYield 62%

Procedure

1.80 g of N-[6-chloro-2-(4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 20 hours under argon in 17 ml of ethylene glycol/water 12:5 in the presence of 0.9 g of potassium hydroxide. The mixture was left to cool and was treated with 140 ml of semi-saturated sodium chloride solution. The mixture was extracted three times with diethyl ether. The combined extracts were washed once with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The brown oil was chromatographed on 50 g of silica gel with dichloromethane/methanol (19:1, then 9:1). The crude product was dissolved in 7 ml of diethyl ether and 0.98 g of fumaric acid was added. The solvent was removed in a vacuum and the residue was recrystallized from 50 ml of chloroform/ethanol 4:1. 1.41 g (62%) of 2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) with m.p. 187°-188° were obtained.

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. extractionThe mixture was extracted three times with diethyl ether
  4. washThe combined extracts were washed once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe brown oil was chromatographed on 50 g of silica gel with dichloromethane/methanol (19:1
  9. dissolutionThe crude product was dissolved in 7 ml of diethyl ether
  10. addition0.98 g of fumaric acid was added
  11. customThe solvent was removed in a vacuum
  12. customthe residue was recrystallized from 50 ml of chloroform/ethanol 4:1

Sources & evidence

ORD record
ord-015fd6120e6c45909c905e8e4c9d14a3
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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