Sodium Hydroxide → 3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Temperature

130 °C

3-Chloropropylamine hydrochloride (VI) (0.2 mol, 39 g) was dissolved into 3N sodium hydroxide solution (containing 10% sodium chloride) and extracted with 300 ml of benzene. The benzene layer was dried over anhydrous magnesium sulfate. Separately, 3-piperidinomethylphenol (V) (0.2 mol, 38.2 g), sodium hydroxide (0.25 mol, 10 g), 100 ml of dimethylsulfoxide, and 70 ml of benzene were charged to a flask equipped with a water quantitative measurement tube, and heated at 130° C. for 3 hours while stirring to remove water produced by the tube, followed by continued stirring for 2 hours at 140°-150° C. To the resulting reaction mixture was dropwise added said benzene solution of 3-chloropropylamine at 150° C. while stirring over 4 hours. The reaction mixture was allowed to stand still to cool to room temperature to separate deposited sodium chloride by filtration. The filtrate was concentrated under reduced pressure and vacuum distilled to obtain 42.7 g of N-[3-(3-aminopropoxy)benzyl] piperidine (VII) (yield: 86.0%). m.p. 148°-151° C./0.25 mmHg.

1. extractionextracted with 300 ml of benzene
2. dry with materialThe benzene layer was dried over anhydrous magnesium sulfate
3. customequipped with a water quantitative measurement tube
4. customto remove water
5. customproduced by the tube
6. stirringby continued stirring for 2 hours at 140°-150° C
7. customTo the resulting reaction mixture
8. additionwas dropwise added
9. customat 150° C.
10. stirringwhile stirring over 4 hours
11. temperatureto cool to room temperature
12. customto separate
13. filtrationby filtration
14. concentrationThe filtrate was concentrated under reduced pressure and vacuum
15. distillationdistilled

ORD record

ord-d6dea37276654251b2438e6ee85053d8

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05317026