Trifluoroacetic acid → HCID 19036427, compound

HRID 264557Notes

Reaction equation

HRID 264557 reaction equation
CO[CH:3](OC)[CH2:4][CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=O.[C:17]([NH:20][CH2:21][CH2:22][NH2:23])(=[O:19])[CH3:18].FC(F)(F)C(O)=O.[OH-].[Na+]>C(O)C.O>[N:23]1([CH2:22][CH2:21][NH:20][C:17](=[O:19])[CH3:18])[CH:3]=[CH:4][C:5]2[CH2:13][C:12]3[C:7]([C:6]1=2)=[CH:8][CH:9]=[CH:10][CH:11]=3

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66082N-(2-aminoethyl)acetamideHCID 19036529HCID 19036529, compound

Product 1

HCID 19036427HCID 19036427, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.7 g of (RS)-2-(2,2-dimethoxyethyl)-1-indanone, 25 g of N-acetylethylenediamine and 30 ml of trifluoroacetic acid in 500 ml of ethanol was boiled under reflux for 96 hours. After cooling and adding 21.5 g of sodium hydroxide in 100 ml of water, the mixture was evaporated to about 100 ml. The mixture was treated with 200 ml of ethyl acetate and washed in succession with 100 ml of saturated sodium chloride solution, 1N hydrochloric acid (4×100 ml), 2N sodium hydroxide solution (4×100 ml) and 100 ml of water. The aqueous washings were extracted with 100 ml of ethyl acetate and the organic phases were combined, dried with magnesium sulfate and evaporated in a vacuum. The residue was purified on basic aluminum oxide (III, dichloromethane) and then on silica gel (ethyl acetate). 0.4 g (22%) of N-[2-(1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethyl]-acetamide was obtained as a colorless solid.

Workup

  1. temperatureunder reflux for 96 hours
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to about 100 ml
  4. additionThe mixture was treated with 200 ml of ethyl acetate
  5. washwashed in succession with 100 ml of saturated sodium chloride solution, 1N hydrochloric acid (4×100 ml), 2N sodium hydroxide solution (4×100 ml) and 100 ml of water
  6. extractionThe aqueous washings were extracted with 100 ml of ethyl acetate
  7. dry with materialdried with magnesium sulfate
  8. customevaporated in a vacuum
  9. customThe residue was purified on basic aluminum oxide (III, dichloromethane)

Sources & evidence

ORD record
ord-593c57745b7c4fe9a9d975282fd31e7c
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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