Morpholine → 3-Morpholino-1-propanol

To a cooled (0° C., ice bath) solution of morpholine (31.5 ml, 0.36 mole) in toluene (300 ml) was added 3-bromopropanol (25 g, 0.18 mole) under argon. The cooling bath was then removed, the resulting mixture was warmed to room temperature, and stirred at room temperature for 1 hr. The mixture was heated at 100° C. (bath temperature) for 3 hrs under argon. After cooling, the mixture was diluted with ethyl acetate. The organic layer was washed (brine), dried (MgSO4), and concentrated. The residue was chromatographed (silica gel, elution by 1:1 CH2Cl2-hexane) to give the title compound as a clear oil.

1. customThe cooling bath was then removed
2. temperatureThe mixture was heated at 100° C. (bath temperature) for 3 hrs under argon
3. temperatureAfter cooling
4. additionthe mixture was diluted with ethyl acetate
5. washThe organic layer was washed (brine)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customThe residue was chromatographed
9. wash(silica gel, elution by 1:1 CH2Cl2-hexane)

ORD record

ord-c6c57f45af7d4f1a9671995ff5c3c0cd

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06548496B2