Sodium Carbonate → HCID 86751672, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(methyl-4-piperidinylamino)-6-benzothiazolol dihydrobromide (0.056 mol) and sodium carbonate (0.142 mol) in N,N-dimethylacetamide (500 ml) was stirred for 1 hour at 60° C. A solution of 1-(4-chlorobutoxy)-4-fluorobenzene (0.061 mol) in N,N-dimethylacetamide (15 ml) was added and the reaction mixture was stirred overnight at 60° C. The cooled reaction mixture was poured out into ice water. This mixture was extracted with toluene. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue (30 g) was purified by column chromatography over silica gel (eluent: CH2 Cl2 /CH3OH 97/3). The pure fractions were collected and the solvent was evaporated. The residue was converted into the (Z)-2-butenedioic acid salt (1:1) in 2-propanol. The precipitate was filtered off and dried, yielding 18 g (58.9%)of 2-[[1-[4-(4-fluorophenoxy)butyl]-4-piperidinyl]methylamino]-6-benzothiazolol (Z)-2-butenedioate(1:1); mp. 180.7° C. (comp. 4).

Provenance & Evidence