N-(2-Aminoethyl)glycine → N-(2-Aminoethyl)glycine

HRID 1529814Notes

Reaction equation

HRID 1529814 reaction equation
O([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][CH:9]=1)C1C=CC=CC=1.[NH2:22][CH2:23][CH2:24][NH:25][CH2:26][C:27]([OH:29])=[O:28]>CO>[NH2:22][CH2:23][CH2:24][NH:25][CH2:26][C:27]([OH:29])=[O:28].[CH:18]1[C:19]2[C:14](=[N:13][C:12]3[C:21]([C:20]=2[NH:22][CH2:23][CH2:24][NH:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 428913N-(2-Aminoethyl)glycineHCID 86725143HCID 86725143, compound

Product 2

HCID 428913N-(2-Aminoethyl)glycineHCID 71513365HCID 71513365, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-((2-Aminoethyl)glycine (4-3) was synthesized following the method reported by Gilon. 2-((2-(Acridin-9-ylamino)ethyl)glycine was synthesized as follows. A mixture of phenoxyacridine (1.35 g, 0.005 mol) and 4-3 (0.65 g, 0.0055 mol) in 20 mL of dry MeOH was refluxed for 36 h. The yellow solid that precipitated during the reaction was collected by filtration, and washed with ethanol and ether, then dried in a vacuum, affording 2.2 g of the product as a yellow solid (Yield: 75%). The structural identity of this compound was confirmed by ESI-MS rather than by NMR spectroscopy due to limited solubility of the compound in common NMR solvents. ESI-MS, +ve mode, m/z [(M+H]+=296.

Workup

  1. temperaturewas refluxed for 36 h
  2. customThe yellow solid that precipitated during the reaction
  3. filtrationwas collected by filtration
  4. washwashed with ethanol and ether
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-5fe364548fe446738e0ccfce456dce62
Source dataset
uspto-grants-2015_07
Patent number
US09090640B2

Reaction notes

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