4-Methylmorpholine → HCID 59007060, compound

Participants

Reaction Steps

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)aniline (D4) (400 mg,1.70 mmol) in dichloromethane (15 ml) was treated with morpholinomethyl-polystyrene HL resin (1.00 g, 3.4 mmol/g loading) followed by 4-bromo-3-fluorobenzenesulfonyl chloride (0.50 ml, 930 mg, 3.40 mmol). The resulting solution was stirred at room temperature for overnight (20 hours). The reaction mixture and was then filtered, washed with methanol, and the solvent evaporated in vacuo. The residue was applied to an SCX column eluting first with methanol and then 2M ammonia in methanol. The fractions containing product were collected, combined and evaporated in vacuo to afford a crude product which was dry loaded onto a column and purified further by chromatography using a Flashmaster with an eluting gradient of 0 to 5% methanol in dichloromethane over 40 mins. Fractions containing product were combined and evaporated in vacuo to afford the title compound (E105). MS (ES+) m/e 472/474 [M+H]+.

Provenance & Evidence