1-(2-Chloroethyl)piperidine → HCID 19834275, compound

HRID 1723353Notes

Reaction equation

HRID 1723353 reaction equation
[Na].[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[C:13]([OH:25])[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:26]1([CH2:32][CH2:33][Cl:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(O)C.C1C=CC=CC=1>[ClH:34].[CH2:2]([O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[C:13]([O:25][CH2:33][CH2:32][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15]2)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 748271-(2-Chloroethyl)piperidineHCID 5360545SodiumHCID 14773084Ethyl 5-Benzyloxy-3-hydroxy-2-naphthoate

Product 1

HCID 19834275HCID 19834275, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

To a stirred solution of 1.4 g (0.062 g atom) of sodium, in 500 cc ethanol, was added 20 g (0.063 mole) of ethyl 5-benzyloxy-3-hydroxy-2-naphthoate. The reaction mixture was warmed to reflux for one hour. 2-Piperidinoethyl chloride (16.2 g 0.11 mole) dissolved in 100 cc of benzene was added dropwise to the reaction mixture. The benzene was removed by azeotropic distillation during which time the reaction volume was maintained at 500 cc by the periodic addition of ethanol. Refluxing was continued for 48 hours. The reaction mixture was filtered and the solvent removed from the filtrate. The residue was treated with water and extracted with ether. The ether solution was washed with water and then dried over anhydrous MgSO4. Hydrogen chloride precipitated the hydrochloride salt which was then crystallized from acetonitrile to yield ethyl 5-benzyloxy-3-(2- piperidinoethoxy)-2-naphthoate hydrochloride, m.p. 163°-6° C. in 38 percent yield (10.8 g).

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for one hour
  3. additionwas added dropwise to the reaction mixture
  4. customThe benzene was removed by azeotropic distillation during which time the reaction volume
  5. temperaturewas maintained at 500 cc by the periodic addition of ethanol
  6. temperatureRefluxing
  7. filtrationThe reaction mixture was filtered
  8. customthe solvent removed from the filtrate
  9. additionThe residue was treated with water
  10. extractionextracted with ether
  11. washThe ether solution was washed with water
  12. dry with materialdried over anhydrous MgSO4
  13. customHydrogen chloride precipitated the hydrochloride salt which
  14. customwas then crystallized from acetonitrile

Sources & evidence

ORD record
ord-db7503c24d664c82ada2d1d2c2e6aa8f
Source dataset
uspto-grants-1989_08
Patent number
US04861795

Reaction notes

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