5-Isothiocyanato-3-methoxymethylisoquinoline → (RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide

Participants

Role	Name	HCID	Charge
Reactant	5-Isothiocyanato-3-methoxymethylisoquinoline	HCID 12874854	—
Reactant	2-(1,2,3,4-Tetrahydroisoquinolin-3-yl)ethan-1-ol	HCID 12874855	—
Solvent	Ethanol	HCID 702	—
Product	(RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide	HCID 12874856	64.9%

Reaction Conditions

Temperature	20 °C

Reaction Steps

5-Isothiocyanato-3-methoxymethylisoquinoline (18.2 g) is added to a solution of (RS)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline (14 g) in ethanol (250 cc). The mixture is stirred for 24 hours at a temperature of about 20° C. The precipitate formed is filtered off and washed with ethanol (2×10 cc) and diethyl ether (2×10 cc). (RS)-3-(2-Hydroxyethyl)-N-(3-methoxymethylisoquinol-5-yl)-1,2,3,4-tetrahydroisoquinoline-2-carbothioamide (20.9 g), m.p. 152° C., is thus obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04261992
Source dataset	uspto-grants-1981_04
ORD ID	ord-3e32b9599e124c32b06419d98519dd9d
Source note	uspto-grants-1981_04