Sodium hydride → HCID 13825040, compound

HRID 648503Notes

Reaction equation

HRID 648503 reaction equation
[H-].[Na+].Cl[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1.[SH:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>CN(C)C=O>[N:23]1[CH:24]=[CH:25][C:20]([S:19][CH:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:11])[CH2:6][CH2:5]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 13825039HCID 13825039, compoundHCID 178418431pyridine-4-thiol

Product 1

HCID 13825040HCID 13825040, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride dispersion in a mineral oil (2.40 g) was slowly added to an ice-cooled solution of phenyl 4-chloro-1-piperidine-carboxylate (15.2 g) and 4-mercaptopyridine (6.66 g) in dry N,N-dimethylformamide (150 ml) with stirring under nitrogen gas. The mixture was stirred at the same temperature for 30 minutes and then at 80° C. for 4.5 hours. The resultant reaction mixture was poured into ice-water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate, and concentrated to dryness in vacuo. The crystalline residue was recrystallized from a mixture of n-hexane and isopropanol to give phenyl 4-[(4-pyridyl)thio]-1-piperidine-carboxylate (15.4 g) as colourless crystals.

Workup

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. customThe resultant reaction mixture
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crystalline residue was recrystallized from a mixture of n-hexane and isopropanol

Sources & evidence

ORD record
ord-55e096191cbf498fa9dbc524d63042ae
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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