7920. Pseudopelletierine
Nomenclature
CAS number: 552-70-5
9-Methyl-9-azabicyclo[3.3.1]nonan-3-one; 9-methyl-3-granatanone; pseudopunicine. C9H15NO; mol wt 153.22.
C 70.55%, H 9.87%, N 9.14%, O 10.44%.
Description and references
In root bark of Punica granatum L., Punicaceae. Extraction procedure: Hess, Eichel, Ber. 50, 380, 1391, 1395 (1917); ibid. 52, 1012 (1919). Synthesis under physiological conditions from calcium acetonedicarboxylate, glutardialdehyde, and methylamine: Menzies, Robinson, J. Chem. Soc. 1924, 2163; cf. Sch"opf, Angew. Chem. 50, 779, 797 (1937). Alternate syntheses: Cope et al., Org. Synth. 37, 73 (1957); Robinson, Hunt, J. Pharm. Pharmacol. 22, 29S (1970); Bottini, Gal, J. Org. Chem. 36, 1718 (1971). Conformation: Chen, LeFevre, J. Chem. Soc. B 1966, 539.
Properties
Orthorhombic prisms from petr ether, mp 54°; bp 246°. Volatile. Strong base. One gram dissolves in about 2.5 ml water, 10 ml ether. Freely sol in alcohol and chloroform; sparingly sol in petr ether.Derivative
Dihydrate.Properties
Plates from water.Derivative
Hydrochloride.C9H15NO.HCl; mol wt 189.68.
C 56.99%, H 8.50%, N 7.38%, O 8.43%, Cl 18.69%.
Properties
Rhombohedra. One gram dissolves in about 1 ml water.Derivative
Sulfate tetrahydrate.2C9H15NO.H2SO4.4H2O; mol wt 476.58.
C 45.36%, H 8.46%, N 5.88%, O 33.57%, S 6.73%.