Sodium Chloride → HCID 19036561, compound

HRID 264460Notes

Reaction equation

HRID 264460 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([N:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH:11]=[CH:10]3)=[C:5]2[CH:4]=1.[OH-:22].[K+].[Cl-].[Na+].[CH2:26]([OH:29])[CH2:27]O.[OH2:30]>>[C:17]([OH:19])(=[O:30])/[CH:18]=[CH:27]/[C:26]([OH:29])=[O:22].[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2=[CH:7][CH:8]=[C:9]3[C:13]([N:12]([CH2:14][CH2:15][NH2:16])[CH:11]=[CH:10]3)=[C:5]2[CH:4]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036494HCID 19036494, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 19036561HCID 19036561, compoundYield 53%

Procedure

211 mg of N-[2-(8-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 9.5 hr. under argon in 3 ml of ethylene glycol/water 2:1 in the presence of 0.25 g of potassium hydroxide. The reaction mixture was left to cool and was poured into 20 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 2 ml of methanol and 70 mg of fumaric acid were added. After the addition of 5 ml of diethyl ether, the crystals were filtered off and recrystallized from 8.5 ml of methanol/DMF 16:1. 142 mg (53%) of 2-(8-methoxy-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) were obtained as white crystals with m.p. 200°-201°.

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 2 ml of methanol
  9. addition70 mg of fumaric acid were added
  10. additionAfter the addition of 5 ml of diethyl ether
  11. filtrationthe crystals were filtered off
  12. customrecrystallized from 8.5 ml of methanol/DMF 16:1

Sources & evidence

ORD record
ord-9e332a8fd6c544fb9a56962cfd2d2ac0
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

Loading…