Ammonium Hydroxide → N-Hydroxy-N-[4-(4-oxo-1-piperidineyl)benzyl]urea
Reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:22]=[CH:21][C:14]([CH2:15][N:16]([OH:20])[C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[NH4+]>Cl>[OH:20][N:16]([CH2:15][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)=[CH:22][CH:21]=1)[C:17]([NH2:19])=[O:18]Participants
4
Procedure
A mixture of N-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzyl]-N-hydroxyurea (2.2 g, 7.16 mmol) (which was obtained in Example 53) and hydrochloric acid (concentrated, 10 mL) was stirred at room temperature for three days. The mixture was then neutralized with ammonium hydroxide, and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (ethyl acetate) gave a white solid (1.86 g, 98% yield); mp 138-140° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.41 (m, 4H), 3.60 (m, 4H), 4.43 (s, 2H), 6.37 (brs, 2H), 7.03 (m, 2H), 7.21 (m, 2H), 9.31 (s, 1H); MS (ES) m/z: 264 (MH+);