Piperidine → Silperisone hydrochloride

HRID 1742632Notes

Reaction equation

HRID 1742632 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][CH2:8][Si:9]([CH3:19])([CH3:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1>C1(C)C(C)=CC=CC=1>[ClH:7].[CH3:8][Si:9]([CH2:19][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 15338764Chloromethyl-dimethyl(4-fluorobenzyl)silane

Product 1

HCID 178567Silperisone hydrochloride

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

After adding 32.7 g of piperidine to a solution containing 32.5 g of chloromethyl-dimethyl-(4-fluorobenzyl)-silane in 40 ml of xylene, the reaction mixture is refluxed for 6 hours under stirring, then the precipitated piperidine hydrochloride is filtered at 20° C. and washed in 3 portions with a total of 60 ml of benzene. The filtrate is combined with the benzene washings and washed in 3 portions with a total of 150 ml of water and the organic phase is dried over anhydrous magnesium sulfate. After filtering the drying agent, the filtrate is evaporated to solvent-free to give the crude named compound as an oily liquid in the base form in a yield of 40 g. This crude product is purified by distillation under reduced pressure to give the title compound in a yield of 36.8 g (92%) with a boiling point of 97°-98° C./0.5 torr.

Workup

  1. temperaturethe reaction mixture is refluxed for 6 hours
  2. filtrationthe precipitated piperidine hydrochloride is filtered at 20° C.
  3. washwashed in 3 portions with a total of 60 ml of benzene
  4. washwashed in 3 portions with a total of 150 ml of water
  5. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  6. filtrationAfter filtering the drying agent
  7. customthe filtrate is evaporated to solvent-free
  8. customto give the crude
  9. distillationThis crude product is purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-ac24912784cd48058403418b9b440eb8
Source dataset
uspto-grants-1994_08
Patent number
US05340823

Reaction notes

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