Potassium Carbonate → 4-[(9,10-Dihydro-9,10-ethanoanthracenyl)methyl]-1-methylpiperazine

Temperature

90 °C

11-Bromomethyl-9,10-dihydro-9,10-ethanoanthracene (0.51 gm), 1-methylpiperazine (1.9 ml) and potassium carbonate (0.20 gm) were combined in hexamethylphosphoramide (5 ml) in a sealed tube and heated to 90° C. for 48 hours. The mixture was extracted between water (25 ml) and ether (50 ml). The ether solution was washed with water (25 ml), then extracted with 3.6 N sulfuric acid (3×25 ml). The combined acid solutions were made basic with the addition of concentrated aqueous ammonia and the resulting mixture was extracted with ether (3×25 ml). The combined ether solutions were dried over magnesium sulfate and the ether removed on a rotary evaporator. The residue was dissolved in anhydrous ether (15 ml) and treated with 3.5% hydrochloric acid in isopropyl alcohol (0.79 ml). The resulting precipitate was filtered, washed with ether (25 ml), and air dried to give the product as a white solid. Analytical data are reported in Table I.

1. extractionThe mixture was extracted between water (25 ml) and ether (50 ml)
2. washThe ether solution was washed with water (25 ml)
3. extractionextracted with 3.6 N sulfuric acid (3×25 ml)
4. additionThe combined acid solutions were made basic with the addition of concentrated aqueous ammonia
5. extractionthe resulting mixture was extracted with ether (3×25 ml)
6. dry with materialThe combined ether solutions were dried over magnesium sulfate
7. customthe ether removed on a rotary evaporator
8. dissolutionThe residue was dissolved in anhydrous ether (15 ml)
9. additiontreated with 3.5% hydrochloric acid in isopropyl alcohol (0.79 ml)
10. filtrationThe resulting precipitate was filtered
11. washwashed with ether (25 ml), and air
12. customdried

ORD record

ord-9884352c3bed41ca9054ae50301aa162

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05192762