N-(2-aminoethyl)acetamide → HCID 19036551, compound

HRID 264547Notes

Reaction equation

HRID 264547 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=O)[CH:9]([CH2:13][CH:14]=O)[CH2:8][CH2:7]2.[C:16]([NH:19][CH2:20][CH2:21][NH2:22])(=[O:18])[CH3:17]>C(O)(=O)C>[Cl:1][C:2]1[C:11]2[C:10]3[N:22]([CH2:21][CH2:20][NH:19][C:16](=[O:18])[CH3:17])[CH:14]=[CH:13][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 19036388HCID 19036388, compound

Product 1

HCID 19036551HCID 19036551, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

325 mg of 8-chloro-2-(2-oxoethyl)-1-tetralone and 290 mg of N-acetylethylenediamine were heated to reflux in 14ml of acetic acid under argon for 1 hour. The solvent was removed in a vacuum and the residue was taken up in 10 ml of water and extracted several times with ethyl acetate. Chromatography on 20 g of silica gel with hexane/ethyl acetate 1:1 and then with ethyl acetate gave 190 mg (45%) of N-[2-(9-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)ethyl]-acetamide as yellowish crystals with m.p. 146°-147°.

Workup

  1. customThe solvent was removed in a vacuum
  2. extractionextracted several times with ethyl acetate

Sources & evidence

ORD record
ord-6506599bb2c14a8e9ed17c6046daae11
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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