Sodium Hydroxide → HCID 86733954, compound

Participants

Reaction Steps

1'-Cyano-4-methoxy-9,10-dihydroanthracene-9-spiro-4'-piperidine (2.3 g.) in dry tetrahydrofuran (20 ml.) is added dropwise with stirring to a solution of lithium aluminium hydride (1 g.) in dry ether (200 ml.). When addition is complete the solution is stirred and heated under reflux for 1 hour. It is then allowed to cool and water (1 ml.), sodium hydroxide solution (1 ml., 2N), water (3 ml.), and ether (100 ml.) are added in succession and the suspension is stirred for 10 minutes and then filtered. The filtrate is washed with water and with brine, dried (MgSO4), and evaporated to give an oil which is taken up in the minimum volume of ethyl acetate and treated with a saturated solution of maleic acid in ethyl acetate. The precipitated solid is collected and recrystallised twice from isopropanol-ether to give 4-methoxy-9,10-dihydroanthracene-9-spiro-4'-piperidine maleate, m.p. 163°-165°C.

Provenance & Evidence