Diethyl Ether → HCID 59693648, compound

Temperature

-10 °C

To a solution of 4-Benzyl-morpholine-2-carbonitrile (10 g, 50 mmol) in dry diethyl ether (100 ml) at −10° C. under an atmosphere of nitrogen was added (time of addition 30 minutes) a solution of 3-fluorophenylmagnesium bromide (0.5N solution in tetrahydrofuran, 120 ml, 60 mmol, 1.2 equivalents, available from Aldrich Chemical Company or Rieke Metals) and the reaction mixture was further stirred at −10° C. for 30 minutes. Then the reaction was allowed to warm to room temperature and stirred for one hour. The reaction was then cooled to 0° C. and quenched by addition of hydrochloric acid (2N aqueous solution, 50 ml) and the resulting mixture was stirred for 30 minutes at 0° C. Then the solution was concentrated in vacuo and the residue was taken-up by sodium hydroxide (2N aqueous solution, 60 ml). The aqueous solution was extracted with diethyl ether, the organics fractions were collected and dried (MgSO4) and the solvent removed under reduced pressure to give the title compound as a brown oil (15 g, 100%). FIA [M+H]+=300.1.

1. temperatureto warm to room temperature
2. stirringstirred for one hour
3. temperatureThe reaction was then cooled to 0° C.
4. customquenched by addition of hydrochloric acid (2N aqueous solution, 50 ml)
5. stirringthe resulting mixture was stirred for 30 minutes at 0° C
6. concentrationThen the solution was concentrated in vacuo
7. extractionThe aqueous solution was extracted with diethyl ether
8. customthe organics fractions were collected
9. dry with materialdried (MgSO4)
10. customthe solvent removed under reduced pressure

ORD record

ord-d426a174c2854f8dacd1ff8334f18750

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354920B2