2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol

• ChemBase ID: 170298
• Molecular Formular: C13H18ClNO2
• Molecular Mass: 255.74052
• Monoisotopic Mass: 255.1026065
• SMILES: C1(NC(C(OC1)(O)c1cc(ccc1)Cl)C)(C)C
• Canonical SMILES: Clc1cccc(c1)C1(O)OCC(NC1C)(C)C
• InChI: InChI=1S/C13H18ClNO2/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3
• InChIKey: RCOBKSKAZMVBHT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol
• IUPAC Traditional name: 2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol
• Synonyms: 2-Hydroxy-2-(3’-chlorophenyl)-3,5,5-trimethylmorpholine; 2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol; Bupropion morpholinol; Hydroxy Bupropion

Database IDs

• CAS Number: 357399-43-0
• PubChem SID: 164226208
• PubChem CID: 9837966

CALCULATED PROPERTIES

• Acid pKa: 10.754683
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.81730276
• LogD (pH = 7.4): 2.479874
• Log P: 2.9009485
• Molar Refractivity: 67.7986 cm^3
• Polarizability: 27.185991 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Acetonitrile; Chloroform; Ethyl Acetate; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 121-123°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H830675

A metabolite of Bupropion, an antidepressant. The compound exists mainly as cyclic acetal (2-hydroxy-2-(3’-chlorophenyl)-355-trimethylmorpholine). See US Pat. # 6342496.

REFERENCES

• Hsyu, P-H., et al.: J. Clin. Pharm., 37, 737 (1997)
• Rotzinger, S., et al.: Cellular & Mol. Neurobiology, 19, 4, 427 (1997)
• US 6342496