SIR 117
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| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}} |
| Chemical and physical data | |
| Formula | C22H26ClN |
| Molar mass | 339.91 g·mol−1 |
| 3D model (JSmol) | |
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SIR 117 is an example of a neuroleptic tranquiliser. The spirocyclic structure is a technological advancement over TCAs such as clomipramine. Chlorination into a molecule is a commonly regarded and well-known method to cause a potentiation in activity. For related compounds see Pramiverine and Chloripramine.
Synthesis
Synthesis:[1] Patent:[2] Starting Precursor:[3]
Ex 6: The Grignard reaction between 3-chlorodibenzosuberone, PC12264964 (1) and methylal (dimethoxymethane) [109-87-5] then chloromethylether was added. The product of this step is claimed to be called 3-chloro-5-hydroxy-5- methoxymethyldibenzosuberane (2). Boiling with formic acid followed by the addition of 1M sulfuric acid led to 3-chloro-5-formyl-dibenzosuberane (3). Intermolecular ring formation occurred upon treatment with methyl vinyl ketone (MVP), and hexamethylphosphoramide to give 3- chlorodibenzosuberaneSpiro[5.5]cyclohex-6-ene-2-one, PC12524381 (4). Catalytic hydrogenation of the olefin led to 3- chlorodibenzosuberaneSpiro[5.5]cyclohex-2-one (5). Ex 17: A modification of the Leuckart reaction using dimethyl ammonium formate completed the synthesis SIR 117 (6).
References
- ↑ Carnmalm, B.; Jacupovic, E.; Johansson, L.; De Paulis, T.; Ramsby, S.; Stjernstrom, N. E.; Renyi, A. L.; Ross, S. B.; Ogren, S. O. (1974). "Antidepressant agents. 1. Chemistry and pharmacology of amino-substituted spiro[5H-dibenzo[a,d]cycloheptene-5,1'-cycloalkanes]". Journal of Medicinal Chemistry. 17 (1): 65–72. doi:10.1021/jm00247a014.
- ↑ Bernt Sigfrid Emanuel Carnmalm, et al., US4053632 (1977 to Astra Lakemedel AB).
- ↑ Winthrop, Stanley O.; Davis, M. A.; Myers, G. S.; Gavin, J. G.; Thomas, R.; Barber, R. (1962). "New Psychotropic Agents. Derivatives of Dibenzo[a,d]-1,4-cycloheptadiene". The Journal of Organic Chemistry. 27 (1): 230–240. doi:10.1021/jo01048a057.
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