ethyl 4-[13-chloro-7-(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: 170827
• Molecular Formular: C23H25ClN2O3
• Molecular Mass: 412.9092
• Monoisotopic Mass: 412.15537035
• SMILES: c12c(C(=C3CCN(CC3)C(=O)OCC)c3c(CC2)cc(cc3)Cl)nccc1CO
• Canonical SMILES: CCOC(=O)N1CCC(=C2c3ccc(cc3CCc3c2nccc3CO)Cl)CC1
• InChI: InChI=1S/C23H25ClN2O3/c1-2-29-23(28)26-11-8-15(9-12-26)21-19-6-4-18(24)13-16(19)3-5-20-17(14-27)7-10-25-22(20)21/h4,6-7,10,13,27H,2-3,5,8-9,11-12,14H2,1H3
• InChIKey: BCKYTUFUNAGTDV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-[13-chloro-7-(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-7-(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-4-(hydroxymethyl)-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene]-1-piperidinecarboxylic Acid Ethyl Ester; 4-Hydroxymethyl Loratadine

Database IDs

• CAS Number: 609806-40-8
• PubChem SID: 164226737
• PubChem CID: 4161540

CALCULATED PROPERTIES

• Acid pKa: 14.78552
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.7646608
• LogD (pH = 7.4): 3.7869375
• Log P: 3.7872295
• Molar Refractivity: 123.7928 cm^3
• Polarizability: 43.71873 Å^3
• Polar Surface Area: 62.66 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Solid
• Melting Point: 96-99°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H947750

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)