3-Azaspiro[5.5]undecane-2,4-dione

To a 100 ml three-neck flask equipped with a thermometer, mechanical stirrer and a reflux condenser was added 1, 1-cyclohexanediaceticacid (1, 10.0 g, 50 mmol) and formamide (4.5 g, 100 mmol). The initial suspension, on heating, became a clear colorless solution and was further heated and stirred at 150–160Cfor 4 h. The hot clear reaction mixture was poured cautiously into water (40 ml). The colorless precipitate obtained was collected, washed with water (10 ml) and dried under vacuum to give 8.80 g (97percent yield) of 2 as a colorless solid (99.9percent purity by HPLC), mp. 168–169C, lit5 169–170C. 1H NMR (300 MHz, DMSO-d6): δ 10.67 (br s, 1H), 2.42 (s, 4H), 1.30–1.41 (m, 10H); 13C NMR (75 MHz, DMSO-d6): δ 172.72, 42.50, 35.29, 32.45, 25.36, 20.97. (M+H)+: Calculated Mass for C10H15NO2 :182.23, Found (ESI-MS):182.21.A flask is charged with 66.5 [G] of acetic anhydride, 66.5 [G] of ammonium acetate, and 100 [G] of 1, 1-cyclohexane diacetic acid. The reaction mass is heated to [160°C-] [170°C] for eight hours, eliminating by distillation the acetic acid that has formed. It is cooled to [90°C-110°C, ] and 200 [G] of water and 100 [G] of secondary butyl alcohol are added. It then undergoes further cooling to room temperature, and the pH is brought to approximately 9 using 30percent of aqueous ammonia. This is followed by filtration, washing the solid with water. 87.7 [G] of dry 3, 3-pentamethylene glutarimide are obtained (yield 97percent).

Molecular Weight:181.23
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:181.110278721
Monoisotopic Mass:181.110278721
Topological Polar Surface Area:46.2
Heavy Atom Count:13
Complexity:223
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes