Reaktion #1468948

Reaktionsgleichung

HCl

9-anthracenecarbaldehyde

2-methyl-2-amino-1,3-propanediol

p-toluenesulfonic acid

NaBH3CN

NaBH3CN

bromocresol green

HCl

→

2-((9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride

Ausbeute 40.0%

Lösungsmittel

EtOH

Et2O

EtOH

H2O

H2O

PhCH3

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was warmed
2. 2
   Temperaturto reflux for a few minutes
3. 3
   workup.ADDITIONdiluted with abs
4. 4
   Sonstigeevery 15 minutes
5. 5
   FiltrationThe precipitate was then collected by filtration through a medium porosity glass fritted funnel
6. 6
   Sonstigepressed dry
7. 7
   WaschenThe filter cake was washed with CH2Cl2 (4×500 mL)
8. 8
   Sonstigesucked dry
9. 9
   Sonstigedried (100°)
10. 10
    SonstigeThe crude solid was recrystallized from EtOH/Et2O (3×)

Vorschrift

To a 2 L Erlenmeyer flask was added 9-anthracenecarbaldehyde (Aldrich Chemical Co., Milwaukee, WI, 53201, 20.63 g, 0.1 mol) 2-methyl-2-amino-1,3-propanediol (Aldrich, 9.13 g, 86.8 mmol), p-toluenesulfonic acid.H2O (Eastman Kodak Co., Rochester, NY, 14650, 0.1 g, 0.5 mmol), and PhCH3 (500 mL). The mixture was warmed to reflux for a few minutes and H2O (2-3 mL) was driven off. The resulting golden colored solution was allowed to cool to RT, diluted with abs. EtOH (500 mL) and stirred overnight. NaBH3CN (Aldrich, 95%, 2.51 g, 42 mmol) was added to the reaction. After the NaBH3CN dissolved, an indicator (bromocresol green, Eastman, 5 mg) was added. To the resulting blue solution was added 5 drops of 1M solution of HCl gas in abs. EtOH every 15 minutes. After 3 days the indicator turned green then yellow and voluminous white precipitate was present in the flask. To the flask was then added 1M HCl gas (10 mL) in abs. EtOH. The reaction was diluted to 4 L with Et2O and stirred for 1 h. The precipitate was then collected by filtration through a medium porosity glass fritted funnel and pressed dry. The filter cake was washed with CH2Cl2 (4×500 mL), pressed and sucked dry, and dried (100°). The crude solid was recrystallized from EtOH/Et2O (3×) to give 13.44 g (40%) of 2-((9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride mp 139°-140° (dec), (C, H, Cl, N).

Quelle