N-(2-aminoethyl)acetamide → N-[2-(7-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethyl]-acetamide

HRID 264436Notes

Reaction equation

HRID 264436 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[CH:9][CH:10]=2)[C:5]1=O.[C:16]([NH:19][CH2:20][CH2:21][NH2:22])(=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:12][C:4]3[CH:3]=[CH:2][N:22]([CH2:21][CH2:20][NH:19][C:16](=[O:18])[CH3:17])[C:5]=32)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 10703357(RS)-2-(2-oxoethyl)-6-methoxy-1-indanone

Product 1

HCID 19036413N-[2-(7-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethyl]-acetamideYield 15.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.5 g of (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone and 2.3 g of N-acetylethylenediamine in 100 ml of toluene was boiled under reflux for 10 minutes. The reaction mixture was evaporated in a vacuum, taken up in dichloromethane, dried with magnesium sulfate and again evaporated. After purification on silica gel (ethyl acetate), 0.9 g (15%) of N-[2-(7-methoxy-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-ethyl]-acetamide was obtained as a yellowish solid.

Workup

  1. temperatureunder reflux for 10 minutes
  2. customThe reaction mixture was evaporated in a vacuum
  3. dry with materialdried with magnesium sulfate
  4. customagain evaporated
  5. customAfter purification on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-4165228171ce491993b72a3510900e6e
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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