N,N-Dimethylaniline → HCID 19748194, compound

Participants

Reaction Conditions

Reaction Steps

Typically a compound of formula (4) is dissolved in an appropriate solvent, such as isopropanol, chlorobenzene, 1,1,1-trichloroethane, toluene, or preferably n-butanol, and about 1-2 molar equivalents, preferably about 1.1 molar equivalents, of the appropriate 3-halopropylamine added, preferably 3-bromopropylamine as its hydrobromide salt, followed by about 1.5 to 4 molar equivalents, preferably about 2.2 molar equivalents, of a tertiary base (such as triethylamine, collidine, N-methylmorpholine, N,N-dimethylaniline or 2,6-lutidine, preferably 2,6-lutidine). The mixture is heated to a temperature of about 80° C. to reflux temperature, preferably about reflux temperature, for about 20 minutes to 4 hours, preferably about 1 hour. A (±)-5,6,9,10,11,12,13,13a-octahydroisoquino[2,1-g][1,6]naphthyridin-8-one derivative, a compound of formula (5), is isolated by conventional means, and purified for example by crystallization from aqueous methanol.

Provenance & Evidence