3-Bromo-1-propanol → 3-(4-Methyl-1-piperazine)propan-1-ol

Temperature

80 °C

1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL). 3-Bromopropanol (2.62 mL, 30 mmol) was added slowly and the mixture was stirred overnight. After heating to 80° C. for 2 h and cooling to r.t., the mixture was filtered and the filter cake was washed thoroughly with toluene. After removal of the toluene, the residue was subjected to Kugelrohr distillation (b.p., 180° C./2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86%). 1H NMR (CDCl3): δ=1.70 (Ψ-quint, J≈5.8 Hz, 2 H), 2.26 (s, 3 H), 2.35-2.6 (m, 8 H), 2.60 (Ψ-t, J=5.8 Hz, 2 H), 3.77 (Ψ-t, J=5.3 Hz, 2 H), 4.09 (s, br., 1 H).

1. temperaturecooling to r.t.
2. filtrationthe mixture was filtered
3. washthe filter cake was washed thoroughly with toluene
4. customAfter removal of the toluene
5. distillationthe residue was subjected to Kugelrohr distillation (b.p., 180° C./2 mbar)

ORD record

ord-078b3b788dea4c689b24e4e0d544d20a

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514460B2