3-(1-METHYL-PIPERIDIN-4-YL)-PROPAN-1-OL Chemical Properties

Boiling point:

114-116 °C(Press: 4 Torr)

Density 

0.929±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

15.16±0.10(Predicted)

3-(1-METHYL-PIPERIDIN-4-YL)-PROPAN-1-OL Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-(1-methylpiperidin-4-yl)-1-propanol from 1-N-BOC-4-piperidinepropionic acid: A. Synthesis of 3-(1-methylpiperidin-4-yl)-propan-1-ol. To a tetrahydrofuran (THF) solution (40 mmol) of 1N lithium aluminum hydride, a THF solution (30 mL) of N-BOC-4-piperidinepropionic acid (3.0 g, 11.6 mmol) was added slowly and dropwise under reflux conditions. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The mixture was further cooled to 0 °C, water (1.5 mL) was slowly added and the reaction mixture was warmed to room temperature within 15 minutes. The mixture was again cooled to 0°C and 10% sodium hydroxide solution (1.5 mL) was slowly added. After warming to room temperature within 15 minutes, the mixture was again cooled to 0°C and additional water (4.5 mL) was added. The resulting mixture was slowly warmed to room temperature over 18 hours and subsequently filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure and the residue was purified by method 2 to give 1.9 g (100% yield) of 3-(1-methylpiperidin-4-yl)-propan-1-ol as a yellow oil. Mass spectrum (electrospray): calculated mass of C9H19NO, 157.15; measured value: 157.15. m/z found, 158.1 [M+H]+. 1H NMR (400MHz, CD3OD): δ 3.45-3.41(m, 2H), 2.77-2.74(m, 2H), 1.89-1.85(m, 2H), 1.64 -1.61(m, 2H), 1.47-1.43(m, 2H), 1.21-1.12(m, 5H).

References

[1] Patent: US2005/70550, 2005, A1. Location in patent: Page/Page column 16-17
[2] Patent: US2005/261309, 2005, A1. Location in patent: Page/Page column 17

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