Water → HCID 59511218, compound

Temperature

-10 °C

To a stirred solution of phenyl ethylene diamine (3 g) taken in dry toluene (50 ml), cooled to −10° C., trimethylaluminum (36 ml, 2M solution in hexane) was added drop wise for 30 minutes. The reaction mixture was brought to room temperature and was heated to 50° C. 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate (8 g) taken in dry toluene (50 ml) added to the above mixture in a drop wise fashion. The combined mixture was stirred at 110° C. for 5 hours, then allowed stir over night at room temperature. To the reaction mixture water (50 ml) was added followed by methanol (50 ml) and allowed to stir for 15 minutes at 0° C. The whole mixture was then filtered through celite bed and washed with chloroform. The combined filtrate was concentrated under reduced pressure. The resulting crude was purified by column chromatography using methanol/chloroform (2:8) as eluent to afford tert-butyl 4-(1-phenyl-4,5-dihydro-1H-imidazol-2-yl)piperidine-1-carboxylate as solid product.

1. customwas brought to room temperature
2. temperaturewas heated to 50° C
3. additionadded to the above mixture in a drop wise fashion
4. stirringallowed stir over night at room temperature
5. stirringto stir for 15 minutes at 0° C
6. filtrationThe whole mixture was then filtered through celite bed
7. washwashed with chloroform
8. concentrationThe combined filtrate was concentrated under reduced pressure
9. customThe resulting crude was purified by column chromatography

ORD record

ord-f4505d411bc54630bc2597b48915d6be

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807671B2