N-(2-aminoethyl)acetamide → HCID 19095277, compound

HRID 486548Notes

Reaction equation

HRID 486548 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].[CH3:8][CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=O)[CH:11]([CH2:20][CH:21]=O)[CH2:10]1>C(Cl)Cl>[CH3:8][CH:9]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[N:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:21]=[CH:20][C:11]=2[CH2:10]1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 53656345HCID 53656345, compound

Product 1

HCID 19095277HCID 19095277, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Acetylethylenediamine (8.1 g) was dissolved in 150 ml of methylene chloride under argon, treated in succession with 140 g of molecular sieve 4 Å and a solution of 14.5 g of 1,2,3,4-tetrahydro-4-methyl-1-oxo-2-naphthaleneacetaldehyde in 100 ml of methylene chloride and heated to reflux for 18 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 19.4 g of dark brown oil, was chromatographed on 300 g of silica gel with ethyl acetate as the eluent. The product, 14.2 g of yellow-brown oil, was dissolved in 200 ml of ethanol, boiled with 0.7 g of Norite® and, after fitration and removal of the solvent, yielded 13.9 g (72%) of N-[2-(4,5-dihydro-5-methyl-1H-benzo[g]indol-1-yl)ethyl]acetamide which was processed without further purification.

Workup

  1. additiontreated in succession with 140 g of molecular sieve 4 Å
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered over a Celite® pad
  5. customThe crude product, 19.4 g of dark brown oil, was chromatographed on 300 g of silica gel with ethyl acetate as the eluent
  6. dissolutionThe product, 14.2 g of yellow-brown oil, was dissolved in 200 ml of ethanol
  7. customafter fitration and removal of the solvent

Sources & evidence

ORD record
ord-c99d66555f774473a8f98a257b6fb6bd
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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