tert-butyl 4-[(5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl]piperidine-1-carboxylate

• ChemBase ID: 165847
• Molecular Formular: C22H31NO5
• Molecular Mass: 389.48524
• Monoisotopic Mass: 389.2202231
• SMILES: c1c(c(cc2c1C(=O)C(C2)CC1CCN(CC1)C(=O)OC(C)(C)C)OC)OC
• Canonical SMILES: COc1cc2c(cc1OC)CC(C2=O)CC1CCN(CC1)C(=O)OC(C)(C)C
• InChI: InChI=1S/C22H31NO5/c1-22(2,3)28-21(25)23-8-6-14(7-9-23)10-16-11-15-12-18(26-4)19(27-5)13-17(15)20(16)24/h12-14,16H,6-11H2,1-5H3
• InChIKey: RXHKMJKBJYEQLX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 4-[(5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl]piperidine-1-carboxylate
• IUPAC Traditional name: tert-butyl 4-[(5,6-dimethoxy-1-oxo-2,3-dihydroinden-2-yl)methyl]piperidine-1-carboxylate
• Synonyms: 4-[(2,3-Dihydro-5,6-dimethoxy-1-oxo-1H-inden-2-yl)methyl]-1-piperidinecarboxylic Acid 1,1-Dimethylethyl Ester; N-Desbenzyl N-tert-butyloxycarbonyl Donepezil

Database IDs

• CAS Number: 948550-60-5
• PubChem SID: 162259980
• PubChem CID: 45356836

CALCULATED PROPERTIES

• Acid pKa: 17.02152
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.383605
• LogD (pH = 7.4): 3.383605
• Log P: 3.383605
• Molar Refractivity: 107.2025 cm^3
• Polarizability: 41.65547 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D288395

A protected impurity of Donepezil (D531750).

REFERENCES

• Dickinson, R., et al.: J. Pharmacol. Exp. Ther., 211, 583 (1979)
• Bartus, R., et al.: Science, 217, 408 (1979)
• Canfell, P., et al.: Drug Metab. Dispos., 14, 703 (1979)
• Chung, B., et al.: Xenobiotica, 24, 451 (1994)