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

1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL). 3-Bromopropanol (2.62 mL, 30 mmol) was slowly and the mixture was stirred overnight at r.t. After heating to 80° C. for 2 h and cooling to r.t., the mixture was filtered and the filter cake was thoroughly washed with toluene. After removal of the solvent, the residue was subjected to distillation (b.p., 180° C./2 mbar) to obtain a colourless oil (4.08 g, 25.8 mmol, 86%). 1H NNR (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. temperatureAfter heating to 80° C. for 2 h
2. temperaturecooling to r.t.
3. filtrationthe mixture was filtered
4. washthe filter cake was thoroughly washed with toluene
5. customAfter removal of the solvent
6. distillationthe residue was subjected to distillation (b.p., 180° C./2 mbar)

ORD record

ord-26036a77677944ababaca33d2aaa7079

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576090B2