1-Bromo-3-chloropropane → Piperidine, 1-(3-chloropropyl)-

A mixture of 1-bromo-3-chloropropane (65.6 g, 0.417 mol) and piperidine (62 ml, 0.625 mol) in anhydrous THF (200 ml) was heated to reflux for 24 h. The mixture was cooled to RT and filtered to remove solids. The organics were concentrated under in vacuo. The resultant residue was taken up in 2N HCl and washed twice with ethyl acetate. The aqueous layer was basicified with 2N NaOH to pH 14. The compound was extracted three times with ethyl acetate and the combined organics dried over anhydrous magnesium sulfate. The solution was then concentrated under reduced pressure to give the desired compound as a yellowish oil.

1. temperaturewas heated
2. temperatureto reflux for 24 h
3. filtrationfiltered
4. customto remove solids
5. concentrationThe organics were concentrated under in vacuo
6. washwashed twice with ethyl acetate
7. extractionThe compound was extracted three times with ethyl acetate
8. dry with materialthe combined organics dried over anhydrous magnesium sulfate
9. concentrationThe solution was then concentrated under reduced pressure

ORD record

ord-abfbc1b7527f4bb1a79b13cadd77ad4b

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557996B2