Sodium hydride → HCID 86739312, compound

HRID 1903229Notes

Reaction equation

HRID 1903229 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:10](=[S:19])[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Cl.[Cl:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1[CH3:31]>CN(C)C=O.O>[ClH:23].[CH3:31][N:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH:25]1[CH2:24][S:19][C:10]1[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 126443922-(Chloromethyl)-1-methylpiperidine--hydrogen chloride (1/1)HCID 132002063-Phenylquinolin-2-thioneHCID 178418361HCID 178418361, compound

Product 1

HCID 86739312HCID 86739312, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.96 g. of a 50% w/w dispersion in mineral oil) was added to a solution of 3-phenylquinolin-2-thione (2.37 g.) in dimethylformamide (100 ml.) at ambient temperature. When all the hydrogen had evolved, 2-chloromethyl-1-methylpiperidine hydrochloride (1.84 g.) was added and the mixture was stirred at ambient temperature for 16 hr. The mixture was then poured into water (750 ml.) and extracted with ethyl acetate (2×150 ml.). The ethyl acetate extract was washed with water (2×50 ml.) and then dried (MgSO4). The solvent was evaporated and the residue was chromatographed on basic alumina (150 g. Brockmann Grade III), eluted with increasing concentrations of chloroform in petroleum ether. The eluate obtained with 20% v/v chloroform in petroleum ether was evaporated. The residue was dissolved in diethyl ether (50 ml.) and ethereal hydrogen chloride was added until precipitation was complete. The solid was collected by filtration and crystallised from ethanol-diethyl ether to give 2-[(1-methyl-2-piperidylmethylthio]-3-phenylquinoline hydrochloride, m.p. 198°-200°.

Workup

  1. extractionextracted with ethyl acetate (2×150 ml.)
  2. extractionThe ethyl acetate extract
  3. washwas washed with water (2×50 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on basic alumina (150 g. Brockmann Grade III)
  7. washeluted
  8. temperaturewith increasing concentrations of chloroform in petroleum ether
  9. customThe eluate obtained with 20% v/v chloroform in petroleum ether
  10. customwas evaporated
  11. dissolutionThe residue was dissolved in diethyl ether (50 ml.)
  12. additionethereal hydrogen chloride was added until precipitation
  13. filtrationThe solid was collected by filtration
  14. customcrystallised from ethanol-diethyl ether

Sources & evidence

ORD record
ord-fe938d146f3044e8bcdf151173172381
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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