1-(3-HYDROXYPROPYL)-4-METHYLPIPERAZINE synthesis
- Product Name:1-(3-HYDROXYPROPYL)-4-METHYLPIPERAZINE
- CAS Number:5317-33-9
- Molecular formula:C8H18N2O
- Molecular Weight:158.24
109-01-3
627-18-9
5317-33-9
General procedure for the synthesis of 1-(3-hydroxypropyl)-4-methylpiperazine from N-methylpiperazine and 3-bromo-1-propanol: Intermediate 7: 3-(4-methylpiperazin-1-yl)-propan-1-ol. Dissolve N-methylpiperazine (6.99 mL, 63 mmol) in toluene (30 mL). 3-Bromo-1-propanol (2.62 mL, 30 mmol) was added slowly and the reaction mixture was stirred at room temperature overnight. Subsequently, the reaction mixture was heated to 80 °C and kept for 2 h, and then cooled to room temperature. The reaction mixture was filtered and the filter cake was washed thoroughly with toluene. After removal of toluene under reduced pressure, the residue was subjected to Kugelrohr distillation (boiling point: 180 °C/2 mbar) to give a colorless oily product (4.08 g, 25.8 mmol, 86% yield). 1H NMR (CDCl3): δ= 1.70 (pseudo quintuple peak, J = 5.8 Hz, 2H), 2.26 (s, 3H), 2.35-2.60 (m, 8H), 2.60 (pseudo triple peak, J = 5.8 Hz, 2H), 3.77 (pseudo triple peak, J = 5.3 Hz, 2H), 4.09 (broad single peak, 1H).
Yield:5317-33-9 86%
Reaction Conditions:
in toluene at 80;
Steps:
Intermediate 7: 3-(4-Methylpiperazin-1-yl)-propan-1-ol.
Intermediate 7: 3-(4-Methylpiperazin-1-yl)-propan-1-ol. 1-Methylpiperazine (6.99 mL, 63 mol) was dissolved in toluene (30 mL). 3-Bromo-propanol (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).
References:
4SC AG EP1674467, 2006, A1 Location in patent:Page/Page column 26
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