N-(2-aminoethyl)acetamide → N-[2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide

HRID 486590Notes

Reaction equation

HRID 486590 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:19]=[C:18]2[C:13]([CH2:14][CH2:15][CH:16]([CH2:21][CH:22]=O)[C:17]2=O)=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][CH2:15][C:16]3[CH:21]=[CH:22][N:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:17]=3[C:18]=2[CH:19]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 19036405(RS)-2-(2-oxoethyl)-7-methoxy-1-tetralone

Product 1

HCID 19036540N-[2-(4,5-dihydro-8-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Acetylethylenediamine (14.5 g) was dissolved in 250 ml of methylene chloride under argon, treated in succession with 250 g of molecular sieve 4 Å and a solution of 28.1 g of 1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthaleneacetaldehyde in 190 ml of methylene chloride and refluxed for 21 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 35.3 g of brown, amorphous material, was chromatographed on 600 g of silica gel with ethyl acetate as the eluent. There were obtained 29.6 g (81%) of N-[2-(4,5-dihydro-8-methoxy-1H-benzo[g]indol-1-yl)-ethyl]acetamide which was processed without further purification.

Workup

  1. additiontreated in succession with 250 g of molecular sieve 4 Å
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered over a Celite® pad
  4. customThe crude product, 35.3 g of brown, amorphous material, was chromatographed on 600 g of silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8375c7061a98479abc3016b4bba7db1f
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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