N-(2-aminoethyl)acetamide → HCID 19036432, compound

HRID 486537Notes

Reaction equation

HRID 486537 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([CH2:20][CH:21]=O)[C:14]2=O>C(Cl)Cl>[Cl:8][C:9]1[C:10]2[CH2:11][CH2:12][C:13]3[CH:20]=[CH:21][N:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:14]=3[C:15]=2[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 540216925-Chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde

Product 1

HCID 19036432HCID 19036432, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Acetylethylenediamine (15.5 g) was dissolved in 300 ml of methylene chloride under argon, treated in succession with 260 g of molecular sieve 4 Å and a solution of 30.8 g of 5-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde in 150 ml of methylene chloride and refluxed for 23 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 37.5 g of brown, amorphous material, 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 29.4 g (74%) of N-[2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethyl]acetamide; m.pt.: 124°-126° C.

Workup

  1. additiontreated in succession with 260 g of molecular sieve 4 Å
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered over a Celite® pad
  4. dissolutionThe crude product, 37.5 g of brown, amorphous material, 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-3bda677a9ea64aea8f761f8939f0d7f9
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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