Methanol → HCID 178461287, compound

Piperazine (54.9 g) and methanol (5 ml) was stirred at 120° C. to melt for 15 minutes. To the solution was dropwise added trans-4-methylcyclohexyl methanesulfonate (33.0 g) and the mixture was stirred at the same temperature for 2 hours. After cooling, to the reaction mixture was added water (150 ml) and extracted three times with a mixture of ethyl acetate (100 ml) and THF (100 ml). The extracts were collected, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (600 ml) eluting with a mixture of dichloromethane, methanol and conc. ammonium hydroxide (4:1:0.1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give cis-1-(4-methylcyclohexyl)piperazine (17.76 g).

1. temperatureAfter cooling, to the reaction mixture
2. extractionextracted three times
3. additionwith a mixture of ethyl acetate (100 ml) and THF (100 ml)
4. customThe extracts were collected
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customThe resulting residue was chromatographed on silica gel (600 ml)
8. washeluting with a mixture of dichloromethane, methanol and conc. ammonium hydroxide (4:1:0.1 v/v)
9. additionThe fractions containing the desired compound
10. customwere collected
11. customevaporated under reduced pressure

ORD record

ord-7da6c985d1e14359b9f60b97733beaa4

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884774B2