Ammonia → 8'-Chloro-3',3'-dimethyl-3',4'-dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indole]

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(5′-chloro-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H)-yl)-2,2-dimethylpropanenitrile (0.81 g, 2.53 mmol ), and wet Raney Nickel (0.88 g), in 2M EtOH.NH3 (60 mL) and THF (10 mL) was hydrogenated in a Parr Hydrogenation Bottle (500 mL) at 56 lb/in2 H2 for 17 hr. The Raney Nickel was removed by filtration through Sulka Floc and the filtrate was poured into a steel pressure vessel and heated at 135° C. for 22 hr. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH, (97/2/1) to give the title compound as an off white solid (0.68 g, 88% yield). Anal. Calc'd for C16H19ClN2O2: C, 62.64; H, 6.24; N, 9.13. Found: C, 62.59; H, 6.19; N, 9.04. NMR (300 Mz, DMSO-d6): consistent; IR: consistent MS: (ES+) m/z 307 [M+H], one Cl pattern observed; m.p.: 121-122° C.

Provenance & Evidence