HCID 53892537, compound → HCID 13753409, compound

A cooled solution of 5.4 grams (0.021 mole) of 5-chloro-3-methoxy-5H-dibenzo[a,d]cycloheptene in 60 milliliters of tetrahydrofuran was added dropwise under an atmosphere of nitrogen to 50 milliliters of a cooled solution of 0.49M 1-methyl-4-piperidylmagnesium chloride in tetrahydrofuran (Grignard solution) over a period of about 40 minutes. After completion of the addition, the mixture was stirred at room temperature for 2 hours and then at reflux temperature for fifteen minutes. The reaction mixture was then cooled and the product recovered from the reaction mixture by concentrating the mixture in vacuo to dryness, adding toluene to dissolve the organic product, filtering off the magnesium, and then separating, washing and drying the toluene solution in a manner similar to that described in Example I. The toluene was vaporized from the dried solution to obtain a residue which was dissolved in acetonitrile, recrystallized therefrom and the crystals dried at 78° C./0.2 mm. Hg over phosphorus pentoxide for four hours to obtain the desired 4-(3-methoxy-5H-dibenzo[a,d]cyclohepten-5 -yl)-1-methylpiperidine product, m.p. 122°-23° C. Elemental analyses were as follows:

1. additionAfter completion of the addition
2. temperatureat reflux temperature for fifteen minutes
3. temperatureThe reaction mixture was then cooled
4. customthe product recovered from the reaction mixture
5. concentrationby concentrating the mixture in vacuo to dryness
6. additionadding toluene
7. dissolutionto dissolve the organic product
8. filtrationfiltering off the magnesium
9. customseparating
10. washwashing
11. dry with materialdrying the toluene solution in a manner similar to
12. customto obtain a residue which
13. customrecrystallized
14. dry with materialthe crystals dried at 78° C./0.2 mm. Hg over phosphorus pentoxide for four hours

ORD record

ord-7066df23046c41489d7e8ad183ea6129

Source dataset

uspto-grants-1986_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04626542