N-(2-aminoethyl)acetamide → HCID 19036565, compound

HRID 486545Notes

Reaction equation

HRID 486545 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([CH2:20][CH:21]=O)[C:16]2=O)=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][CH2:14][C:15]3[CH:20]=[CH:21][N:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:16]=3[C:17]=2[CH:18]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 54188933HCID 54188933, compound

Product 1

HCID 19036565HCID 19036565, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Acetylethylenediamine (2.9 g) was dissolved in 50 ml of methylene chloride under argon, treated in succession with 4.5 g of molecular sieve 4 Å and a solution of 5.7 g of 7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde in 20 ml of methylene chloride and heated to reflux for 16 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 6.6 g of brown solid, was dissolved in a 6-fold amount of hot ethyl acetate and, after the addition of an 8-fold amount of hexane, boiled briefly. There were obtained 4.0 g (55%) of N-[2-(8-chloro-4,5-dihydro-1H-benzo[g]indol-1-yl)ethyl]acetamide; m.pt.: 144°-146° C.

Workup

  1. additiontreated in succession with 4.5 g of molecular sieve 4 Å
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered over a Celite® pad
  5. dissolutionThe crude product, 6.6 g of brown solid, was dissolved in a 6-fold amount of hot ethyl acetate
  6. additionafter the addition of an 8-fold amount of hexane

Sources & evidence

ORD record
ord-8268d3d2bc1d4496b349a14de4788e4e
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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