Sodium Chloride → HCID 19036524, compound

HRID 264566Notes

Reaction equation

HRID 264566 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[C:14]3[N:13]([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-:22].[K+].[Cl-].[Na+].[CH2:26]([OH:29])[CH2:27]O.[OH2:30]>>[C:19]([OH:21])(=[O:30])/[CH:20]=[CH:27]/[C:26]([OH:29])=[O:22].[CH3:1][O:2][C:3]1[C:15]2[C:14]3[N:13]([CH2:16][CH2:17][NH2:18])[CH:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036609HCID 19036609, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 19036524HCID 19036524, compoundYield 61%

Procedure

2.3 g of N-[2-(4,5-dihydro-9-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 16 hours under argon in 23 ml of ethylene glycol/water 2:1 in the presence of 2.70 g of potassium hydroxide. The reaction mixture was left to cool and was poured into 200 ml of semi-concentrated sodium chloride solution. The mixture was extracted three times with diethyl ether and 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 methanol and treated with 0.93 g of fumaric acid. The separated crystals were recrystallized from a total of 70 ml of methanol. 1.76 g (61%) of 2-(4,5-dihydro-9-methoxy-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) were obtained as yellowish crystals with m.p. 184°-185°.

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 methanol
  9. additiontreated with 0.93 g of fumaric acid
  10. customThe separated crystals were recrystallized from a total of 70 ml of methanol

Sources & evidence

ORD record
ord-edb6936bc8ff4b72926174f522e725ec
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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