1,4-Dioxane hydrochloride → HCID 89924032, compound

Temperature

25 °C

To a solution of (R)-tert-butyl 4-(3-cyanocyclopent-2-en-1-yl)piperazine-1-carboxylate (13 g, 46.9 mmol) in dry dichloromethane (30 ml) was added slowly hydrochloric acid 1,4 dioxane (100 ml, 4M solution) in a drop wise manner 0° C. The reaction mixture was stirred at 25° C. for 3 h. The progress of the reaction was monitored by TLC. The reaction mixture was then concentrated under reduced pressure. The residue was diluted with dichloromethane (100 ml) and treated with methanolic ammonia (50 ml, 7M solution) and stirred for 30 minutes. The reaction mixture was then evaporated under reduced pressure to obtain crude product which was purified by flash column chromatography over silica gel (100-200 mesh) using 10% methanol in dichloromethane as an eluent to obtain title compound ((7 g, 84%).

1. concentrationThe reaction mixture was then concentrated under reduced pressure
2. additionThe residue was diluted with dichloromethane (100 ml)
3. additiontreated with methanolic ammonia (50 ml, 7M solution)
4. stirringstirred for 30 minutes
5. customThe reaction mixture was then evaporated under reduced pressure
6. customto obtain crude product which
7. customwas purified by flash column chromatography over silica gel (100-200 mesh)

ORD record

ord-5bc63acd48cf4379a53d16f0dc67ce1e

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359367B2