Water → HCID 19036504, compound

HRID 264550Notes

Reaction equation

HRID 264550 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13]3[N:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH:11]=[CH:10][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:20]=1.[OH-:21].[K+].[OH2:23].[Cl-].[Na+].[CH2:26]([OH:29])[CH2:27]O.O>>[C:17]([OH:19])(=[O:23])/[CH:18]=[CH:27]/[C:26]([OH:29])=[O:21].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13]3[N:12]([CH2:14][CH2:15][NH2:16])[CH:11]=[CH:10][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:20]=1

Participants

6

Reactant 5

HCID 962WaterHCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036582HCID 19036582, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 19036504HCID 19036504, compoundYield 58%

Procedure

0.5 g of N-[7-chloro-2-(4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]-acetamide was heated to 140° for 22 hours under argon in 4.5 ml of ethylene glycol/water 2:1 in the presence of 0.25 g of potassium hydroxide. The mixture was left to cool and was treated with 40 ml of water and 10 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 30 ml of diethyl ether and added dropwise to a suspension of 208 mg of fumaric acid in 30 ml of diethyl ether. The solvent was removed in a vacuum and the residue was recrystallized from 75 ml of ethanol/ethyl acetate 3:2. 355 mg (58%) of 2-(7-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) with m.p. 176°-177° 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 30 ml of diethyl ether
  9. additionadded dropwise to a suspension of 208 mg of fumaric acid in 30 ml of diethyl ether
  10. customThe solvent was removed in a vacuum
  11. customthe residue was recrystallized from 75 ml of ethanol/ethyl acetate 3:2

Sources & evidence

ORD record
ord-37dedf4f89e549e5a454e452dbacbd69
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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