Claims
- 1. A process for preparing an R- or S-norbenzomorphane of formula 1 ##STR4## wherein R.sup.1 is H, C.sub.1-8 alkoxy, hydroxy or halogen, which comprises the steps of converting a 4-methylene-piperidine derivative of formula 2 ##STR5## (where R.sup.2 is R.sup.1) with an acid into the corresponding acid addition salt,
- reacting said corresponding acid addition salt in a reaction medium with an aluminum (III) halide at a temperature in the range from about 0.degree. C. to about 150.degree. C., and isolating the R- or S-norbenzomorphane of formula 1.
- 2. The process according to claim 1 wherein the aluminum (III) halide is aluminum tribromide or aluminum trichloride.
- 3. The process according to claim 1, wherein the reaction medium is a mono- or polychlorinated alkane having 1 to 3 carbon atoms, a chlorinated benzene or benzene derivative or an amide of a C1-3-carboxylic acid or a mixture of such.
- 4. The process according to claim 1, where the reaction medium is dichloromethane, 1,2-dichloroethane, chlorobenzene or dimethylacetamide or a mixture of such.
- 5. The process according to claim 1, wherein the reaction is carried out at a temperature in the range from about 20 to about 150.degree. C.
- 6. The process according to claim 4, wherein the reaction is carried out at a temperature in the range from about 40 to about 70.degree. C.
- 7. The process according to claim 1, wherein about 2 to about 12 equivalents of aluminum (III) halide are used, based on the educt.
- 8. The process according to claim 7, wherein about 3 to about 10 equivalents of aluminum (III) halide are used, based on the educt.
- 9. The process according to claim 8, wherein about 3 to about 5 equivalents of aluminum (III) bromide or aluminum (III) chloride are used, based on the educt.
- 10. The process according to claim 1, where (+)-2-(3-methoxyphenyl)methyl-3,3-dimethyl-4-methylene-piperidine is used as the piperidine derivative.
- 11. The process according to claim 1, where (-)-2-(3-methoxypheneyl)methyl-3,3-dimethyl-4-methylene-piperidine is used as the piperidine derivative.
- 12. The process according to claim 1, where the piperidine derivative is used in the form of an addition salt with a mineral acid.
- 13. The process according to claim 12, wherein the piperidine derivative used is in the form of an addition salt with a hydrohalic acid or sulphuric acid.
- 14. The process according to claim 13, wherein the piperidine derivative used is in the form of an addition salt with hydrochloric or hydrobromic acid.
- 15. The method as recited in claim 1 where R.sup.2 is alkoxy further comprising the step of converting the alkoxy to hydroxy through ether splitting by reacting with a hydrohalic acid.
Priority Claims (1)
Number |
Date |
Country |
Kind |
198 22 822 |
May 1998 |
DEX |
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Parent Case Info
This application claims benefit under U.S.C. .sctn. 119 (e) of U.S. Provisional Application No. 60/092,893, filed Jul. 15, 1998.
US Referenced Citations (4)