Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 979375Generated: October 30, 2026

Sodium borohydride → 3-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline

https://huagongshe.com/reaction/979375

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium borohydrideHCID 4311764—
Reactant3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-3,4-dihydroisoquinolinium iodideHCID 20202211—
SolventMethanolHCID 887—
Product3-(4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhex-1-yl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolineHCID 129102—

Reaction Steps

The resulting compound of formula 41 is then hydrogenated to produce a compound of formula 1. This hydrogenation is preferably performed using NaBH4. The solvent used is preferably a lower alkanol, particularly MeOH. The reaction is carried out at a temperature of about -10° C. to about 50° C., preferably about 0° C., over about 10 minutes to about 3 hours, preferably 1 hour. For example, 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-3,4-dihydroisoquinolinium iodide (41) is suspended in MeOH at 0° C., then treated with NaBH4 for about 1 hour to produce 3-[4-(3,4-dimethoxyphenyl)-4-isopropyl-4-cyanobutyl]-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04667038
Source datasetuspto-grants-1987_05
ORD IDord-3e0d27dc110e4f999382de9521095820
Source noteuspto-grants-1987_05