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1
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Rx-ID: 32108216 Find similar reactions
23%
in acetonitrile
T=20 - 40°C; Inert atmosphere; Hide Experimental Procedure
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RESEARCH TRIANGLE INSTITUTE; UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, C/O NATIONAL INSTITUTES OF HEALTH, OFFICE OF TECHNOLOGY TRANSFER; BLOUGH, Bruce E.; ROTHMAN, Richard; LANDAVAZO, Antonio; PAGE, Kevin M.; DECKER, Ann Marie
Patent: WO2011/146850 A1, 2011 ; Location in patent: Page/Page column 52 ; Title/Abstract Full Text Show Details
1:
A 0.4 M solution of 2-bromo-l-(3-fluorophenyl)propan-l-one (3.05g, leq) in acetonitrile (33mL) was mixed in a l OOmL round bottom flask under N2 (g). Ethanolamine (1.6mL, 2eq) was added and stirred/refluxed for 6 hrs at 40°C. After cooling to room temperature overnight the volatiles were removed under reduced pressure, the residue was then taken up in ethyl acetate, washed with saturated sodium bicarbonate (3 x 50mL), brine (2 x 50mL), and dried over anhydrous sodium sulfate. After filtration the volatiles were removed under reduced pressure affording 1.464g (53percent) of crude product. Purified on 12g column (ISCO) using a system of methylene chloride (A)/methanol (B) with a 20-30percent gradient (B). Fractions 13-32 were collected and concentrated under reduced pressure affording 0.638 g (23percent) of purified product. The free base was salted with 0.3506g of fumaric acid and recrystalized using methanol/ethyl acetate yielding 0.5672g of final product.
2
Synthesize Find similar Multi-step reaction with 2 steps 1: bromine / dichloromethane / 20 °C 2: acetonitrile / 20 - 40 °C / Inert atmosphere View Scheme
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Rx-ID: 32108218 Find similar reactions
RESEARCH TRIANGLE INSTITUTE; UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, C/O NATIONAL INSTITUTES OF HEALTH, OFFICE OF TECHNOLOGY TRANSFER; BLOUGH, Bruce E.; ROTHMAN, Richard; LANDAVAZO, Antonio; PAGE, Kevin M.; DECKER, Ann Marie
Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details