Isoquinoline, 3,4-dihydro-1-((3,4-bis(1-methylethoxy)phenyl)methyl)-6,7-diethoxy-, hydrochloride → 1-({3,4-Bis[(propan-2-yl)oxy]phenyl}methyl)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Participants

Reaction Steps

21 g (0.0455 mole) of 6,7-diethoxy-1-(3',4'-diisopropoxybenzyl)-3,4-dihydroisoquinoline hydrochloride was dissolved in 300 ml of methanol in a 1 liter 3-necked flask. The solution was cooled in an ice/water bath and 2.1 g (0.0555 moles) of sodium borhydride was added in two portions with agitation. Stirring was continued for half an hour, the solvent removed under reduced pressure and the residue obtained taken up in 500 ml of diethyl ether. The ethereal solution was washed 3 times with 200 ml of water, dried over sodium sulphate and the solvent removed under reduced pressure. The oil obtained was dissolved in 20 ml of isopropyl ether, and allowed to crystallize. The product was filtered and re-dissolved in 200 ml of diethyl ether, then a solution of hydrochloric acid in diethyl ether added to pH 2. The solvent was removed under reduced pressure and the residue obtained triturated, firstly in isopropyl ether and then in diethyl ether. After drying, 19.5 g of the title hydrochloride was obtained. Yield=92.5%, m.p. 168° C.

Provenance & Evidence