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

HRID 2255821노트

반응식

HRID 2255821 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 1496691,3-Propanediol, 2-((1-fluoranthenylmethyl)amino)-2-methyl-, hydrochloride수율 43.8%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0f348aa2a47a46e38bb98ff83cb50904
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05241107

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