ethyl 4-[13-chloro-5-(hydroxymethyl)-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]piperidine-1-carboxylate

• ChemBase ID: 170826
• Molecular Formular: C23H25ClN2O3
• Molecular Mass: 412.9092
• Monoisotopic Mass: 412.15537035
• SMILES: c12c(C(=C3CCN(CC3)C(=O)OCC)c3c(CC2)cc(cc3)Cl)nc(cc1)CO
• Canonical SMILES: CCOC(=O)N1CCC(=C2c3ccc(cc3CCc3c2nc(CO)cc3)Cl)CC1
• InChI: InChI=1S/C23H25ClN2O3/c1-2-29-23(28)26-11-9-15(10-12-26)21-20-8-6-18(24)13-17(20)4-3-16-5-7-19(14-27)25-22(16)21/h5-8,13,27H,2-4,9-12,14H2,1H3
• InChIKey: XTEULJRKHVVHLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-[13-chloro-5-(hydroxymethyl)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]piperidine-1-carboxylate
• IUPAC Traditional name: ethyl 4-[13-chloro-5-(hydroxymethyl)-4-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]piperidine-1-carboxylate
• Synonyms: 4-[8-Chloro-5,6-dihydro-2-(hydroxymethyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene]-1-piperidinecarboxylic Acid Ethyl Ester; 2-Hydroxymethyl Loratadine

Database IDs

• CAS Number: 609806-39-5
• PubChem SID: 164226736
• PubChem CID: 29981724

CALCULATED PROPERTIES

• Acid pKa: 14.25794
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.8572993
• LogD (pH = 7.4): 3.8685558
• Log P: 3.8687015
• Molar Refractivity: 123.2706 cm^3
• Polarizability: 43.719845 Å^3
• Polar Surface Area: 62.66 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol; THF
• Apperance: White Solid
• Melting Point: 76-78°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H947745

A usual impurity in Loratadine syrup formulations, a nonsedating-type histamine H1-receptor.

REFERENCES

• Okamoto, T., et al.: Chem. Pharm. Bull ., 7, 130 (1959)
• Eyjolfsson, R., et al.: Pharmazie, 58, 154 (1959)