1-(2-BROMO-ETHYL)-PIPERIDINE HYDROBROMIDE

4.0 g of 3-aminoindazole prepared by the method described in C. E. KWARTLER et. al., J. Am. Chem. Soc., 65, 1804 (1943), 8.18 g of 1-(2-bromoethyl)piperidine hydrobromide obtained from Referential Example 1, 8.28 g of anhydrous potassium carbonate and 80 ml of dried N, N-dimethylformamide were mixed and stirred for 24 hours at 80 C. After the reaction mixture was condensed under reduced pressure, 100 ml of chloroform and 50 ml of water were added to the condensed residue. Then the chloroform layer was separated, dried with anhydrous sodium sulfate and chloroform was removed under reduced pressure.General procedure: Unless otherwise stated, N-substituted sulfonohydrazides were made by the following method. A suspension of N'-((5-cyanopyrazolo[1, 5-a]pyridin-3-yl)methylene)-2-methyl-5-nitrobenzenesulfonohydrazide (3) (20 mg, 0.052 mmol), Br(CH2)2NR2·HBr (2 equiv) and Cs2CO3 (5 equiv) in DMF (3 mL) was stirred at room temperature for 2 h. The solution was diluted with water, extracted with CH2Cl2, the extracts were dried (Na2SO4) and the solvents removed in vacuo. Chromatography (eluting with a CH2Cl2:MeOH gradient) gave the substituted hydrazide.15 g of the 1-(2-phenoxyethyl)piperidine thus obtained was reacted with 30 ml of 40% hydrobromic acid at 150 C. for 7 hours with stirring. The reaction solution was cooled, added with 20 ml of chloroform and then the chloroform layer was separated. The hydrobromic acid layer was condensed under reduced pressure and the residue was recrystallized from 5 ml of ethyl alcohol to give 15.1 g of 15 g of the 1-(2-phenoxyethyl)piperidine thus obtained was reacted with 30 ml of 40% hydrobromic acid at 150 C. for 7 hours with stirring. The reaction solution was cooled, added with 20 ml of chloroform and then the chloroform layer was separated. The hydrobromic acid layer was condensed under reduced pressure and the residue was recrystallized from 5 ml of ethyl alcohol to give 15.1 g of

Molecular Weight:273.01
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:272.95508
Monoisotopic Mass:270.95712
Topological Polar Surface Area:3.2
Heavy Atom Count:10
Complexity:69.3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes