1-Bromopropane → HCID 178459264, compound

A mixture of NaH (60% susp., 1.4 mmol) and ethylene glycol dimethylether (3 mL) was added cyclohexyl-cis-(4-hydroxycyclohexyl)-amine (0.36 mmol) and the mixture was stirred under N2 at rt for 5 min followed by addition of propylbromide (5.5 mmol). The mixture was refluxed for 18 h under N2. The reaction mixture was cooled to rt and quenched with anhydrous EtOH (0.5 mL). The mixture was filtered and the residue was extracted with ethylene glycol di-methylether (2 mL). The organic phase was evaporated to dryness under reduced pressure and co-evaporated with toluene (10 LI). The residue was added HCl in MeOH (1.25 M, 5 mL) and evaporated under reduced pressure affording a white solid. The solid was washed with TBME (2 mL) and dissolved in a mixture of DCM (5 mL) and 1 M aqueous NaOH (5 mL). The organic phase was washed with H2O (5 mL), dried (Na2SO4), and evaporated under reduced pressure to give the desired cyclohexyl-cis-(4-propoxycyclohexyl)amine as an oil which was used in the next step without further purification.

1. temperatureThe mixture was refluxed for 18 h under N2
2. temperatureThe reaction mixture was cooled to rt
3. customquenched with anhydrous EtOH (0.5 mL)
4. filtrationThe mixture was filtered
5. extractionthe residue was extracted with ethylene glycol di-methylether (2 mL)
6. customThe organic phase was evaporated to dryness under reduced pressure and co-evaporated with toluene (10 LI)
7. additionThe residue was added HCl in MeOH (1.25 M, 5 mL)
8. customevaporated under reduced pressure
9. customaffording a white solid
10. washThe solid was washed with TBME (2 mL)
11. dissolutiondissolved in a mixture of DCM (5 mL) and 1 M aqueous NaOH (5 mL)
12. washThe organic phase was washed with H2O (5 mL)
13. dry with materialdried (Na2SO4)
14. customevaporated under reduced pressure

ORD record

ord-377a96409dfe44aabf92639ca45e390c

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582769B2