Sodium Chloride → HCID 19036559, compound

HRID 264551Notes

Reaction equation

HRID 264551 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][N:11]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C:12]=3[C:4]=2[CH:3]=1.[OH-:21].[K+].[Cl-].[Na+].[CH2:25]([OH:28])[CH2:26]O.[OH2:29]>>[C:16]([OH:18])(=[O:29])/[CH:17]=[CH:26]/[C:25]([OH:28])=[O:21].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][N:11]([CH2:13][CH2:14][NH2:15])[C:12]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036565HCID 19036565, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 19036559HCID 19036559, compoundYield 45%

Procedure

1.0 g g of N-[8-chloro-2-(4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]-acetamide was heated to 140° for 24 hours under argon in 7.5 ml of ethylene glycol/water 2:1 in the presence of 0.50 g of potassium hydroxide. The mixture was left to cool and was poured into 75 ml of ice-water. After the addition of 25 ml of 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 crude product was dissolved in 20 ml of diethyl ether and added dropwise to a suspension of 406 mg of fumaric acid in 80 ml of diethyl ether. The solvent was removed in a vacuum and the residue was recrystallized from 90 ml of ethanol/ethyl acetate 5:4. 556 mg (45%) of 2-(8-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) with m.p. 179°-180° were obtained as white crystals.

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. dissolutionThe crude product was dissolved in 20 ml of diethyl ether
  9. additionadded dropwise to a suspension of 406 mg of fumaric acid in 80 ml of diethyl ether
  10. customThe solvent was removed in a vacuum
  11. customthe residue was recrystallized from 90 ml of ethanol/ethyl acetate 5:4

Sources & evidence

ORD record
ord-79ecc6e3d8fc4ead8c464d930f39144e
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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