Trifluoromethanesulfonic acid → HCID 13920595, compound

HRID 569205Notes

Reaction equation

HRID 569205 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([CH:10]2[CH:15]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH2:14][CH2:13][CH2:12][NH:11]2)=O)[CH2:4][CH2:3]1.FC(F)(F)S(O)(=O)=O>>[F:24][C:20]1[CH:21]=[CH:22][C:23]2[C:8](=[C:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[CH2:16][CH2:17][C:18]=2[CH:19]=1

Participants

3

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 20148818HCID 20148818, compound

Product 1

HCID 13920595HCID 13920595, compoundYield 38%

Procedure

A solution of (1-methyl-4-piperidinyl)[3-[2-(3-fluorophenyl)ethyl]-2-piperidinyl]methanone (15.0 g, 0.046 mole) in 74 mL (125.5 g, 0.837 mole) of trifluoromethanesulfonic acid is stirred at ambient temperature for 18 hours. The reaction is quenched with ice-water and the solution made basic with potassium hydroxide. The product is extracted into ethyl acetate. The ethyl acetate solution is filtered to remove insolubles and the filtrate is concentrated to a residue. Following purification by silica gel chromatography, 5.4 g (0.0175 mole) of product is obtained in 38% yield.

Workup

  1. customThe reaction is quenched with ice-water
  2. extractionThe product is extracted into ethyl acetate
  3. filtrationThe ethyl acetate solution is filtered
  4. customto remove insolubles
  5. concentrationthe filtrate is concentrated to a residue
  6. custompurification by silica gel chromatography

Sources & evidence

ORD record
ord-189722dad6644dd8a6ab93610b5cf63d
Source dataset
uspto-grants-1988_03
Patent number
US04731447

Reaction notes

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