Sodium Chloride → HCID 19036541, compound

HRID 264558Notes

Reaction equation

HRID 264558 reaction equation
[N:1]1([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[CH:5]=[CH:4][C:3]2[CH2:6][C:7]3[C:12]([C:2]1=2)=[CH:11][CH:10]=[CH:9][CH:8]=3.[OH-:19].[K+].[Cl-].[Na+].[CH2:23]([OH:26])[CH2:24]O.[OH2:27]>COC(C)(C)C>[C:16]([OH:18])(=[O:27])/[CH:17]=[CH:24]/[C:23]([OH:26])=[O:19].[N:1]1([CH2:13][CH2:14][NH2:15])[CH:5]=[CH:4][C:3]2[CH2:6][C:7]3[C:12]([C:2]1=2)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 19036427HCID 19036427, compoundHCID 20437942Ethylene glycol water

Product 1

HCID 19036541HCID 19036541, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

385 mg of N-[2-(1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethyl]-acetamide were heated to 140° for 22 hours under argon in 6 ml of ethylene glycol/water 2:1 in the presence of 540 mg of potassium hydroxide. The mixture was left to cool and was treated with 20 ml of semi-saturated sodium chloride solution. The mixture was extracted three times with diethyl ether and the combined extracts were dried over sodium sulfate, filtered and evaporated. The brown oil was dissolved in 5 ml of methanol and treated with 185 mg of fumaric acid, whereby pale brown crystals separated. These were dissolved in 50 ml of warm methanol. After cooling to room temperature, the product was crystallized by the slow addition of 50 ml of diethyl ether. The product obtained was heated in 15 ml of tert.-butyl methyl ether for 1 hour, filtered off under suction and dried in a vacuum. 220 mg (53%) of 2-(1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethylamine fumarate with m.p. 201°-202° were obtained.

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. extractionThe mixture was extracted three times with diethyl ether
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe brown oil was dissolved in 5 ml of methanol
  8. additiontreated with 185 mg of fumaric acid, whereby pale brown crystals
  9. customseparated
  10. dissolutionThese were dissolved in 50 ml of warm methanol
  11. customthe product was crystallized by the slow addition of 50 ml of diethyl ether
  12. customThe product obtained
  13. filtrationfiltered off under suction
  14. customdried in a vacuum

Sources & evidence

ORD record
ord-d79d0eb4a0e94283863af7239cf3641c
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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