HCID 68818181, compound → 3-Chloro-4-[2-(4-methylpiperidin-1-yl)ethoxy]phenylamine

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N+:18]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([CH3:17])[CH2:13][CH2:12]1>C1COCC1.[H][H].[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([CH3:17])[CH2:15][CH2:16]1

Participants

Procedure

6.90 g (23.1 mmol) of 3-chloro-4-[2-(4-methylpiperidin-1-yl)ethoxy]nitrobenzene (III.1.b) are dissolved in 100 mL of THF and hydrogenated for 8 hours at ambient temperature at a pressure of 20 psi with hydrogen and 3.0 g of Raney nickel as catalyst. Then the catalyst is filtered off, the solvent is eliminated, and the residue is purified through a silica gel column with a gradient of methylene chloride/methanol (33:1 to 9:1) as eluant. Yield: 3.66 g (59% of theory); Rf value: 0.50 (silica gel, methylene chloride/methanol=9:1); C14H21ClN2O; EII mass spectrum: m/z=269/271 [M+H]+.