N-(2-aminoethyl)acetamide → HCID 19095320, compound

HRID 486534Notes

Reaction equation

HRID 486534 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])[CH3:2].O=[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH:10]1[CH2:19][CH:20]=O>C(OCC)C>[N:7]1([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:12][CH2:11][C:10]=2[CH:19]=[CH:20]1

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 12216680HCID 12216680, compound

Product 1

HCID 19095320HCID 19095320, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Molecular sieve 4 Å and 14.9 g of N-acetylethylenediamine (200 g) was added in succession under argon to a solution of 27.5 g of 1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde in 275 ml of diethyl ether. The reaction mixture was stirred at boiling temperature for 5 hours and subsequently cooled. The molecular sieve was filtered off, the filtrate was freed from solvent and the crude product was chromatographed on 600 g of silica gel with ethyl acetate as the eluent. There were obtained 23.5 g (79%) of N-[2-(4,5-dihydro-1H-benzo[g]indol-1-yl)ethyl]-acetamide with a melting point of 95°-96° C. (ethyl acetate).

Workup

  1. customfor 5 hours
  2. temperaturesubsequently cooled
  3. filtrationThe molecular sieve was filtered off
  4. customthe crude product was chromatographed on 600 g of silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-79a81e1754ee4a489cc793513a299ead
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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