Sodium Hydroxide → HCID 13049055, compound

Reaction equation

[N+]([NH:4][C:5]([NH2:7])=[O:6])([O-])=O.[N:8]1([CH2:14][CH2:15][O:16][CH:17]2[CH2:21][CH2:20]N[CH2:18]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[OH-].[Na+]>C(O)C>[N:8]1([CH2:14][CH2:15][O:16][CH:17]2[CH2:21][CH2:20][N:4]([C:5]([NH2:7])=[O:6])[CH2:18]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Procedure

Nitrourea (7.3 g., 0.055 mole of 80% wet reagent) and 3-(2-piperidinoethoxy)pyrrolidine were stirred together in 100 ml. ethanol at reflux for 2 hr. After cooling, the reaction mixture was filtered and the filtrate concentrated to give 12.5 g. solid material which was determined by nuclear magnetic resonance spectrum analysis to be a salt. The crude product was treated with dilute sodium hydroxide solution and the free base extracted into chloroform twice. The chloroform extracts were combined, washed with water, dried over magnesium sulfate, filtered, and concentrated to give 6.8 g. of off-white solid product. Recrystallization from isopropyl ether-isopropanol gave 3.7 g. (30.7%) white solid, m.p. 133.5°-135.5° C.