Reaktion #548630

Reaktionsgleichung

N-(Chloromethyl)piperidine

butyl lithium

2-piperidinomethylnaphthalene

water

→

2,3-Bis(piperidinomethyl)naphthalene dihydrochloride

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturunder reflux for 1 hour
3. 3
   ExtraktionThe precipitated material was extracted into ether
4. 4
   Waschenthe extract was washed with water
5. 5
   Trocknendried over anhydrous magnesium sulphate
6. 6
   Sonstigeevaporated to dryness
7. 7
   SonstigeThe residue was purified by chromatography on silica
8. 8
   workup.ADDITIONan ethereal solution of the product was treated with ethereal hydrogen chloride
9. 9
   Sonstige1,2-Bis(piperidinomethyl)naphthalene dihydrochloride crystallised from propan-2-ol as prisms, m.p. 240°

Vorschrift

To a stirred solution of 2-piperidinomethylnaphthalene (5.6 g) in dry ether (200 ml) was added, under nitrogen, a 1.5M ethereal solution of butyl lithium (18.3 ml) and the mixture was kept at room temperature for 24 hours. N-(Chloromethyl)piperidine (7.34 g) was added, the mixture was heated under reflux for 1 hour, and poured into water (1 l). The precipitated material was extracted into ether, the extract was washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was purified by chromatography on silica and an ethereal solution of the product was treated with ethereal hydrogen chloride. 1,2-Bis(piperidinomethyl)naphthalene dihydrochloride crystallised from propan-2-ol as prisms, m.p. 240°.

Quelle