Potassium Carbonate → HCID 13825029, compound

HRID 648497Notes

Reaction equation

HRID 648497 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 793424-chloro-N-methylpiperidineHCID 5202162-Fluorothiophenol

Product 1

HCID 13825029HCID 13825029, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloro-1-methylpiperidine (110.1 g), 2-fluorothiophenol (117.3 g), and potassium carbonate (170.8 g) in N,N-dimethylformamide (1.0 l) was stirred at 90° C. for 2 hours and filtered. The filtrate was concentrated in vacuo to give an oily residue, which was diluted with brine and extracted three times with diethyl ether. The extracts were dried over magnesium sulfate, concentrated in vacuo, and distilled to give 4-[(2-fluorophenyl)thio]-1-methylpiperidine (111.1 g) as a yellow oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customto give an oily residue, which
  4. extractionextracted three times with diethyl ether
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationdistilled

Sources & evidence

ORD record
ord-893fad7111c3425b9e8754a2dc15e0b1
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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