Dimethyl Sulfoxide → 2-Anilinocyclohexanol

Temperature

90 °C

A 15 mL screw top test tube fitted with a PTFE septum cap was purged with argon before addition of CuI (5.0 mg, 0.026 mmol, 2.6 mol %), NaOH (83.0 mg, 2.08 mmol) and rac-2-amino-1-cyclohexanol HCl (158 mg, 1.04 mmol). Iodobenzene (139 μL, 1.25 mmol), dimethyl sulfoxide (670 μL), and a stock solution of 9.45 M NaOH (330 μL, 3.12 mmol) were added, via syringe, under argon. The septum cap was replaced with a solid, Teflon-lined cap and the reaction was stirred magnetically at 90° C. for 48 h. The resulting homogeneous solution was allowed to cool before dilution with 10 mL brine. The reaction mixture was transferred to a separatory funnel and extracted with diethyl ether (3×10 mL). The organic extracts were washed with 3 M HCl (3×10 mL). The acid extracts were then cooled in an ice bath and the solution was basified using a saturated NaOH solution. When the pH of the solution became basic, as indicated by pH paper, the solution became opaque. The mixture was transferred to a separatory funnel and extracted with methylene chloride (3×10 mL). The organic extract was washed with brine, dried over MgSO4 and concentrated. A pale yellow oil was obtained and placed under high vacuum overnight. While under vacuum the oil solidified to give 182.5 mg (92% yield) of an off-white solid, mp 57–58° C.

1. customcap
2. customThe septum cap
3. customlined cap
4. customThe reaction mixture was transferred to a separatory funnel
5. extractionextracted with diethyl ether (3×10 mL)
6. washThe organic extracts were washed with 3 M HCl (3×10 mL)
7. temperatureThe acid extracts were then cooled in an ice bath
8. customThe mixture was transferred to a separatory funnel
9. extractionextracted with methylene chloride (3×10 mL)
10. extractionThe organic extract
11. washwas washed with brine
12. dry with materialdried over MgSO4
13. concentrationconcentrated
14. customA pale yellow oil was obtained
15. customplaced under high vacuum overnight

ORD record

ord-58b01c49a3104bfc9b7152273b88da44

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07115784B2