N-(2-aminoethyl)acetamide → HCID 19036609, compound

HRID 264565Notes

Reaction equation

HRID 264565 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11](=O)[CH:10]([CH2:14][CH:15]=O)[CH2:9][CH2:8]2.[C:17]([NH:20][CH2:21][CH2:22][NH2:23])(=[O:19])[CH3:18]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:12]2[C:11]3[N:23]([CH2:22][CH2:21][NH:20][C:17](=[O:19])[CH3:18])[CH:15]=[CH:14][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 19036394HCID 19036394, compound

Product 1

HCID 19036609HCID 19036609, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

400 mg of 8-methoxy-2-(2-oxoethyl)-1-tetralone were heated to reflux for 15 minutes under argon with 205 mg of N-acetyl-ethylenediamine in 8 ml of toluene. The solvent was removed in a vacuum and the residue was chromatographed on 40 g of silica gel with hexane/ethyl acetate 1:1 and then with ethyl acetate. 280 mg (54%) of N-[2-(4,5-dihydro-9-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were obtained as yellowish crystals with m.p. 132°-133°.

Workup

  1. customThe solvent was removed in a vacuum
  2. customthe residue was chromatographed on 40 g of silica gel with hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-b77e62632b1747f8a5b23aef6a1e5090
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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