Diethylaminoethyl chloride → HCID 12291137, compound

Participants

Reaction Steps

A mixture of 10 parts of 1-(4-chlorophenyl)-4,5-dihydro-1H-benz[g]indazole-3-carboxylic acid, 5parts of 2-diethylaminoethyl chloride and 160 parts of anhydrous 2-propanol is heated at reflux for 16 hours. The 2-propanol is then removed under reduced pressure and the resulting residue is partitioned in ether and dilute hydrochloric acid. The aqueous layer is separated and washed twice with ether. It is then made alkaline with cold aqueous sodium hydroxide solution and then extracted with ether. The combined ether extracts are dried over potassium carbonate and the solvent is evaporated to leave a residual free base. This is recrystallized from a mixture of benzene and hexane to give 2-diethylaminoethyl 1-(4-chlorophenyl)-4,5-dihydro-1H-benz[g]indazole-3-carboxylate melting at about 102°-103°C.

Provenance & Evidence