2-Chlorobenzaldehyde → 1-(2-Chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

To a mixture of 2-chlorobenzaldehyde (0.5 M in dichloromethane) (800 μl) and 2-(3,4-dimethoxy-phenyl)-ethylamine (0.25 M in dichloromethane) (800 μl) was added trifluoroacetic acid (150 μl). The mixture was shaken at room temperature for 12-24 hours then evaporated to dryness. Toluene (1 ml) was added the mixture vortexed and re-evaporated to dryness. The residue was dissolved in methanol (1.5 ml) and dichloromethane (1 ml) and filtered through a SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid). The cartridge was washed with methanol (3 ml) the product eluted with 0.5 M ammonia solution (5 ml). Product containing fractions were combined and evaporated to dryness. Toluene (1 ml) was added the mixture vortexed and re-evaporated to dryness to give 1-(2-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline which was used directly in the next step.

1. customthen evaporated to dryness
2. additionToluene (1 ml) was added the mixture
3. customre-evaporated to dryness
4. dissolutionThe residue was dissolved in methanol (1.5 ml)
5. filtrationdichloromethane (1 ml) and filtered through a SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid)
6. washThe cartridge was washed with methanol (3 ml) the product
7. washeluted with 0.5 M ammonia solution (5 ml)
8. additionProduct containing fractions
9. customevaporated to dryness
10. additionToluene (1 ml) was added the mixture
11. customre-evaporated to dryness

ORD-Eintrag

ord-2af2c301f8a948af88608ea1a6f7ed04

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08343961B2