Phenol → HCID 13048757, compound

A mixture of phenol (46.5 g), 1-(2-chloroethyl) piperidine (103.5 g), and potassium carbonate (207 g) in dimethylformamide (900 mL) was heated to reflux. After refluxing for two hours, the reaction mixture was allowed to cool to room temperature. This mixture was filtered, and the solids washed with dimethylformamide (100 mL). The combined filtrates was concentrated in vacuo to a brown oil. This oil was dissolved with ethyl acetate (400 mL), and the resulting solution was washed with water (2×200 mL) and saturated brine (2×200 mL). The ethyl acetate solution was dried over magnesium sulfate, filtered, and concentrated in vacuc to a brown oil. This oil was dissolved in methanol (100 mL), and the resulting solution acidified with 3% methanolic hydrochloric acid (prepared from acetyl chloride and methanol, 500 mL). The resulting solution was evaporated to dryness in vacuo. The residue (74 g) was crystallized from 1-propanol (800 mL) and ethyl acetate (500 mL) to give 59.6 g of the title compound as an off-white crystalline solid. Melting point 179-180° C.

1. temperaturewas heated to reflux
2. temperatureAfter refluxing for two hours
3. filtrationThis mixture was filtered
4. washthe solids washed with dimethylformamide (100 mL)
5. concentrationThe combined filtrates was concentrated in vacuo to a brown oil
6. dissolutionThis oil was dissolved with ethyl acetate (400 mL)
7. washthe resulting solution was washed with water (2×200 mL) and saturated brine (2×200 mL)
8. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuc to a brown oil
11. dissolutionThis oil was dissolved in methanol (100 mL)
12. customThe resulting solution was evaporated to dryness in vacuo
13. customThe residue (74 g) was crystallized from 1-propanol (800 mL) and ethyl acetate (500 mL)

ORD record

ord-485e7b247540482c85954cba9777ef40

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06008377