Thionyl Chloride → 1-Benzyl-2-(chloromethyl)piperidine

HRID 538662Notes

Reaction equation

HRID 538662 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2735486(1-Benzylpiperidin-2-yl)methanol

Product 1

HCID 150154541-Benzyl-2-(chloromethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of compound 13 (3.6 g, 15.00 mmol) in chloroform (50 mL) was added thionyl chloride (1.34 mL) at 0° C. The reaction mixture was heated at reflux for 2 hours and then concentrated. The residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane to provide compound 14 as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with saturated sodium bicarbonate solution, water and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography on 230-400 mesh silica gel eluting with 10% EtOAc-hexane

Sources & evidence

ORD record
ord-411c250c3a24456caa4a517d6cf6d979
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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