Sodium Chloride → HCID 19036607, compound

HRID 264538Notes

Reaction equation

HRID 264538 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:14]3[N:13]([CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:21]=1.[OH-:22].[K+].[Cl-].[Na+].[CH2:26]([OH:29])[CH2:27]O.[OH2:30]>>[C:18]([OH:20])(=[O:30])/[CH:19]=[CH:27]/[C:26]([OH:29])=[O:22].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:14]3[N:13]([CH2:15][CH2:16][NH2:17])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:21]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036463HCID 19036463, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 19036607HCID 19036607, compoundYield 38%

Procedure

0.5 g of N-[2-(4,5-dihydro-7-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 23 hours under argon in 21 ml of ethylene glycol/water 2:1 in the presence of 0.60 g of potassium hydroxide. The reaction mixture was left to cool and poured into 100 ml of semi-concentrated 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 solution of 245 mg of fumaric acid in 20 ml of methanol. The mixture was left to stir for one hour. and the yellowish crystals were filtered off under suction. 241 mg (38%) of 2-(4,5-dihydro-7-methoxy-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:0.8) with m.p. 195° were obtained.

Workup

  1. waitThe reaction 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 solution of 245 mg of fumaric acid in 20 ml of methanol
  10. waitThe mixture was left
  11. filtrationand the yellowish crystals were filtered off under suction

Sources & evidence

ORD record
ord-23f710f75060437ab1ee074daaf4de10
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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