Potassium Iodide → 6-Methoxy-2-(4-methoxy-phenyl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline

N-(4-Methoxy-phenyl)-N-[2-(3-methoxyphenyl)-ethyl]-acetamide (0.60 g) was heated to 80° C. in phosphorus oxychloride (8.4 mL) for 24 h. The reaction was cooled then poured slowly onto ice (150 mL). Potassium iodide (0.65 g) was added. After 30 min, the mixture was extracted with methylene chloride (2×50 mL). The organic extracts were dried over sodium sulfate, filtered through celite and concentrated. The resulting residue was dissolved in methanol (21 mL) and sodium borohydride (0.23 g) was added slowly in small portions. After 18 h the solvent was removed under reduced pressure. The residue was partitioned between water (100 mL) and ethyl acetate (50 mL) and the aqueous layer was extracted with ethyl acetate (25 mL). The combined organic extracts were dried over sodium sulfate, filtered through celite and concentrated giving the title compound MS: 284.3 (MH+); HPLC tR; 2.11 min (method D).

1. temperatureThe reaction was cooled
2. additionthen poured slowly onto ice (150 mL)
3. extractionthe mixture was extracted with methylene chloride (2×50 mL)
4. dry with materialThe organic extracts were dried over sodium sulfate
5. filtrationfiltered through celite and
6. concentrationconcentrated
7. dissolutionThe resulting residue was dissolved in methanol (21 mL)
8. additionsodium borohydride (0.23 g) was added slowly in small portions
9. customAfter 18 h the solvent was removed under reduced pressure
10. customThe residue was partitioned between water (100 mL) and ethyl acetate (50 mL)
11. extractionthe aqueous layer was extracted with ethyl acetate (25 mL)
12. dry with materialThe combined organic extracts were dried over sodium sulfate
13. filtrationfiltered through celite
14. concentrationconcentrated

ORD record

ord-76f11030f194407a814935ddbab2b6b2

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07256201B2