13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-ol

• ChemBase ID: 170441
• Molecular Formular: C19H19ClN2O
• Molecular Mass: 326.81996
• Monoisotopic Mass: 326.11859092
• SMILES: C1(=C2CCNCC2)c2c(CCc3c1ncc(c3)O)cc(cc2)Cl
• Canonical SMILES: Oc1cnc2c(c1)CCc1c(C2=C2CCNCC2)ccc(c1)Cl
• InChI: InChI=1S/C19H19ClN2O/c20-15-3-4-17-13(9-15)1-2-14-10-16(23)11-22-19(14)18(17)12-5-7-21-8-6-12/h3-4,9-11,21,23H,1-2,5-8H2
• InChIKey: NDFMTPISBHBIKE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-ol
• IUPAC Traditional name: 13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-6-ol
• Synonyms: 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-3-ol; 3-Hydroxydesloratadine; Sch 45581; 3-Hydroxy Desloratadine; 8-Chloro-6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine; N-Methyl Desloratadine

Database IDs

• CAS Number: 38092-89-6; 119410-08-1
• PubChem SID: 164226351
• PubChem CID: 10359050

CALCULATED PROPERTIES

• Acid pKa: 8.818947
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.49522007
• LogD (pH = 7.4): 1.7305418
• Log P: 2.8889081
• Molar Refractivity: 103.0197 cm^3
• Polarizability: 35.96062 Å^3
• Polar Surface Area: 45.15 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Brown Solid; Light Brown Solid
• Melting Point: 116-118°C; 169-171°C

Safety Information

• Storage Condition: -20°C Freezer; -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M316500

An intermediate in the synthesis of Loratadine. Loratadine impurity.

Toronto Research Chemicals - H936750

An active metabolite of Loratadine.

REFERENCES

• Zhong, D., et al.: Pharmazie, 49, 736 (1994)
• Mayer, B., et al.: J. Chromatogr., 907, 21 (1994)
• Ruperez, F., et al.: J. Pharm. Biomed. Anal., 29, 35 (1994)
• Batenhorst, R., et al.: Eur. J. Clin. Pharmacol., 31, 247 (1986)
• Hickman, D., et al.: Drug Metab. Dispos., 26, 207(1986)
• Lin, Y., et al.: Drug Metab. Dispos., 29, 368 (2001)