Piperidine → Silperisone hydrochloride

HRID 1614552Notes

Reaction equation

HRID 1614552 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 filtration 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 name 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. filtrationThe filtration
  5. washwashed in 3 portions with a total of 150 ml of water
  6. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  7. filtrationAfter filtering the drying agent
  8. customthe filtrate is evaporated to solvent-free
  9. customto give the crude name compound as an oily liquid in the base form in a yield of 40 g
  10. distillationThis crude product is purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-427bd83639ef405eb68394b22be8e628
Source dataset
uspto-grants-1993_03
Patent number
US05198446

Reaction notes

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