DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God
DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution
n

Sunday, 30 August 2015

Nucleophilic Aromatic Substitution of 5-fluoro-1-indanone with morpholine ......5-morpholino-1-indanone




5-Morpholino-1-indanone
.

Nucleophilic Aromatic Substitution of 5-fluoro-1-indanone with morpholine

 The synthesis was performed using standard Schlenk techniques under a nitrogen atmosphere.  To a dried and nitrogen flushed glass microwave reaction vial was added  5-flouro-1-indanone (0.101 g, 0.67 mmol).  The vial's atmosphere was cycled four times. Morpholine (2.0 mL, 0.023 mol, 3.47 equivs.) was added, The reaction was then sealed and heated to 100 oC for 20 hours under variable watt microwave heating.  At the completion of the reaction the crude material was transferred to a 50 mL round bottom flask using 3.5 mL ethyl acetate. Silica and ethyl acetate (4.5 mL) were added to the flask and the solvent was removed under reduced pressure to yield a free flowing dry load.  The crude product was then subjected to purification via flash chromatography (75 : 25 ethyl acetate : hexanes) to yield a red solid (144 mg, 98.7%).

1H NMR:  (CDCl3) δ ppm 2.59-2.62 (m, 2H), 3.01 (t, J=5.7 Hz, 2H), 3.30 (t, J=5.0 Hz, 4H), 3.83 (t, J=4.7 Hz, 4H), 6.78 (m, 6.78-6.79, 1H), 6.83-6.86 (m, 1H), 7.61 (d, J=8.8 Hz, 1H).

13C NMR:  (CDCl3) δ ppm 25.8, 36.3, 47.6, 66.4, 109.7, 114.0, 124.9, 128.2, 155.8, 157.7, 204.9

GCMS EI [M+]  Predicted: 217.2, Actual: 217


see


5-morpholino-1-indanone-1H.pdf
5-morpholino-1-indanone-13C.pdf
GCMS Data 5-morpholino-1-indanone.pdf

GCMS EI [M+]  Predicted: 217.2, Actual: 217


HELP TO INTERPRET USING RELATED 
MOLECULES.....U CAN LEARN

SOME OTHER INDANONES
Chern, C.-Y.; Yek, Y.-L.; Chen, Y.-L.; Kan, W.-M. J. Chin. Chem. Soc. 200855, 846–853.
Dinges, J.; Albert, D.H.; Arnold, L.D.; Ashworth, K.L.; et al J. Med Chem. 2007, 50, 2011-2029

 

2D NMR Workshop 2011
The resonance assignment of 2-ethyl-1-indanone 










References

Chern, C.-Y.; Yek, Y.-L.; Chen, Y.-L.; Kan, W.-M. J. Chin. Chem. Soc. 2008, 55, 846–853.

Dinges, J.; Albert, D.H.; Arnold, L.D.; Ashworth, K.L.; et al J. Med Chem. 2007, 50, 2011-2029

No comments:

Post a Comment