Water → HCID 59511173, compound

Temperature

-10 °C

To tert-butyl 4-[(2-aminoethyl)amino]piperidine-1-carboxylate (6 g) taken in dry toluene (50 ml) cooled to −10° C., trimethylaluminium was added slowly in dry toluene under nitrogen atmosphere. Reaction mixture was allowed to warm to r.t. and a second lot of solution of tert-butyl 4-[(2-aminoethyl)amino]piperidine-1-carboxylate (6 g in 50 ml of toluene) was added very slowly to it. The combined mixture was heated up to 55° C. for 30 minutes. A solution of ethyl benzoate (7.4 g in 50 ml of dry toluene) was added very-very slowly to the reaction mixture at 55° C. over a period of 40 minutes. After the completion of addition, the reaction mixture was refluxed for over night. Reaction mixture was cooled to 0° C. and water (3×50 ml) was added. The combined mixture was filtered through celite pad. The filtrate was concentrated under reduced pressure and the resulting oil was purified by column chromatography to afford tert-butyl 4-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)piperidine-1-carboxylate as a pure product.

1. customReaction mixture
2. temperatureto warm to r.t.
3. temperatureThe combined mixture was heated up to 55° C. for 30 minutes
4. additionAfter the completion of addition
5. temperaturethe reaction mixture was refluxed for over night
6. customReaction mixture
7. temperaturewas cooled to 0° C.
8. filtrationThe combined mixture was filtered through celite pad
9. concentrationThe filtrate was concentrated under reduced pressure
10. customthe resulting oil was purified by column chromatography

ORD record

ord-7e680dfc494b40c59eccf0498a716f97

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807676B2