Methylamine → trans-1,2,3,4-Tetrahydro-1-methylamino-2-(pyrrolidin-1-yl)naphthalene

Participants

Reaction Steps

A solution of 10.8 g of the product of Step A, 100 ml of tetrahydrofuran and 9.7 ml of triethylamine was cooled to -20° C. and then over 10 minutes, 5.5 ml of methanesulfonyl chloride were added. The precipitate was allowed to return to ambient temperature and then 38 ml of methylamine at 33% in ethanol were added. The mixture was stirred for 20 hours and the tetrahydrofuran and the ethanol were eliminated under reduced pressure at 50° C. 100 ml of water and 10 ml of a solution of sodium hydroxide were added and extraction was done with methylene chloride. The extracts were washed with water, dried, filtered and concentrated to dryness to obtain 11.5 g of the expected product as a brown oil.

Provenance & Evidence