N-(2-aminoethyl)acetamide → HCID 19036582, compound

HRID 486541Notes

Reaction equation

HRID 486541 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[CH:14]([CH2:20][CH:21]=O)[CH2:13][CH2:12]2>C(Cl)Cl>[Cl:8][C:9]1[CH:18]=[CH:17][C:16]2[C:15]3[N:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:21]=[CH:20][C:14]=3[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 54535871HCID 54535871, compound

Product 1

HCID 19036582HCID 19036582, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Acetylethylenediamine (2.4 g) was dissolved in 40 ml of methylene chloride under argon, treated in succession with 40 g of molecular sieve 4 Å and a solution of 4.8 g of 6-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde in 20 ml of methylene chloride and refluxed for 40 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 5.6 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 4.2 g (67%) of N-[2-(7-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]acetamide; m.pt.: 144°-145° C.

Workup

  1. additiontreated in succession with 40 g of molecular sieve 4 Å
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered over a Celite® pad
  4. dissolutionThe crude product, 5.6 g of brown solid, was dissolved in a 6-fold amount of hot ethyl acetate
  5. additionafter the addition of an 8-fold amount of hexane

Sources & evidence

ORD record
ord-a8e0f524730b4fea86a7871a7432352b
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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