Ethanol → 1,3-Propanediol, 2-((1-fluoranthenylmethyl)amino)-2-methyl-, hydrochloride

HRID 2255821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2255821
[Cl:1][CH2:2][C:3]1[C:17]2=[C:18]3[C:10]([C:11]4[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:9][CH:8]=[CH:7][C:6]3=[CH:5][CH:4]=1.[NH2:19][C:20]([CH3:25])([CH2:23][OH:24])[CH2:21][OH:22].C([O-])([O-])=O.[K+].[K+].CCO>O.Cl>[ClH:1].[C:3]1([CH2:2][NH:19][C:20]([CH3:25])([CH2:23][OH:24])[CH2:21][OH:22])[C:17]2=[C:18]3[C:10]([C:11]4[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:9][CH:8]=[CH:7][C:6]3=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 15312-Amino-2-methyl-1,3-propanediolHCID 11430Potassium CarbonateHCID 152291Fluoranthene, 1-(chloromethyl)-

Produkt 1

HCID 1496691,3-Propanediol, 2-((1-fluoranthenylmethyl)amino)-2-methyl-, hydrochlorideAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a RB flask equipped with magnetic stirring bar, condenser and N2 inlet line with bubbler was added crude 1-chloromethylfluoranthene (3C, 13.01 g, 52 mmol), 2-amino-2-methyl-1,3-propanediol (Aldrich, 5.46 g, 52 mmol), K2CO3 (MCB, 14.37 g, 0.104 mol) and abs. EtOH (300 mL). The reaction was stirred at reflux overnight, filtered hot, and the solvent removed by rotary evaporation to give a crude dark oil. This was acidified with 1N HCl and dissolved in H2O, filtered, basified with 5N NaOH solution and filtered to give a crude white solide. The material was dissolved in ethanolic HCl solution, filtered and precipitated with Et2O. Filtration followed by crystallization (abs. EtOH/Et2O, 1:4) gave after filtration and drying a 43.8% yield of 2-[(1-fluorantheneylmethyl)amino]-2-methyl-1,3-propanediol hydrochloride 0.3 H2O, mp 185-188 (dec), (C,H,N,Cl).

Aufarbeitung

  1. customTo a RB flask equipped with magnetic stirring bar, condenser and N2 inlet line with bubbler
  2. temperatureat reflux overnight
  3. filtrationfiltered hot
  4. customthe solvent removed by rotary evaporation
  5. customto give a crude dark oil
  6. filtrationfiltered
  7. filtrationfiltered
  8. customto give a crude white solide
  9. filtrationfiltered
  10. customprecipitated with Et2O
  11. filtrationFiltration
  12. customfollowed by crystallization (abs. EtOH/Et2O, 1:4)
  13. customgave
  14. filtrationafter filtration

Quellen und Nachweise

ORD-Eintrag
ord-0f348aa2a47a46e38bb98ff83cb50904
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05241107

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