1-Chloro-2-nitrobenzene → HCID 53923744, compound

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Reaction Steps

The 4-(2-aminophenyl)piperazine-1-carbaldehyde can be prepared by reacting 1-chloro-2-nitrobenzene with piperazine-1-carbaldehyde to give 4-(2-nitro-phenyl)piperazine-1-carbaldehyde and then reducing. The reaction between the 1-carbaldehyde and the 2-nitrobenzene is carried out in a suitable solvent (e.g., DMF, NMP, acetonitrile, any appropriate mixture of suitable solvents, etc., preferably DMF) at 50° to 100° C., typically at 60° to 80° C. and preferably at approximately 100° C., and requires 20° to 50 hours. The reduction can be effected with a suitable chemical reducing agent (e.g., nickel boride, stannous chloride, etc., preferably nickel boride) in a suitable solvent, typically an alcohol (e.g., ethanol, methanol, isopropanol, any appropriate mixture of alcohols, etc.) and preferably methanol, at 20° to 65° C., typically at 50° to 65° C. and preferably at approximately 60° C., requiring 1to 20 hours. Alternatively, the reduction can be effected under a hydrogen atmosphere at 0 to 50 psi, typically at 10 to 20 psi and preferably at approximately 15 psi, with a suitable catalyst (e.g., 10% palladium on carbon (10% Pd/C), palladium hydroxide, palladium acetate, etc. preferably 10% Pd/C) and in an appropriate solvent, typically an alcohol (e.g., ethanol, methanol, isopropanol, any appropriate mixture of alcohols, etc.) and preferably methanol, at 20° to 50° C., typically at 23° to 27° C. and preferably at 25° C., requiring 5 to 40 hours. Further details of the reaction steps set forth in this and the preceding paragraph are provided in Example 17, infra.

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