Water → HCID 20280626, compound

HRID 1248027Notes

Reaction equation

HRID 1248027 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][C:11]1([CH:18]2SCCCS2)[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1.[OH2:24].B(F)(F)F>O1CCCC1.CCOCC>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][C:11]1([CH:18]=[O:24])[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 6356Boron trifluorideHCID 13476054HCID 13476054, compound

Product 1

HCID 20280626HCID 20280626, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound 4-(2-fluorophenylmethoxy)-1-methyl-4-(1,3-dithian-2-yl)piperidine hydrochloride (5 g, 13.1 mmole) was suspended in tetrahydrofuran (50 ml), and water (5 ml) was added to completely dissolve the compound. Red mercuric oxide (8.6 g, 39.7 mmole) was added to the solution. After a complex was formed, BF3 etherate (32.3 ml, 39.7 mmole) was added dropwise to the stirred suspension under nitrogen and reaction was taken to completion as indicated by TLC. The reaction mixture was diluted with an equal volume of ether and filtered. The filtrate was treated with saturated potassium carbonate to form a precipitate. The mixture was extracted with ethyl acetate, and the ethyl acetate extracts were washed with saturated brine. The washed extract was dried over anhydrous potassium carbonate, filtered and taken to dryness. The residue was dissolved in ether from which the hydrochloride was precipitated. The resulting material was recrystallized from ethyl acetate/ethanol. After filtration, washing with ethyl acetate and ether, the product was air-dried to yield 1.3 g (4.5 mmole, 36.9%) of 4-(2-fluorophenylmethoxy)-1-methyl-4-oxomethyl piperidine hydrochloride. MS (MH+ =252), NMR (CDCl3) and IR (CHCl3) were consistent with the structure, mp=164°-167° C.

Workup

  1. dissolutionto completely dissolve the compound
  2. customAfter a complex was formed
  3. customreaction
  4. filtrationfiltered
  5. additionThe filtrate was treated with saturated potassium carbonate
  6. customto form a precipitate
  7. extractionThe mixture was extracted with ethyl acetate
  8. washthe ethyl acetate extracts were washed with saturated brine
  9. extractionThe washed extract
  10. dry with materialwas dried over anhydrous potassium carbonate
  11. filtrationfiltered
  12. dissolutionThe residue was dissolved in ether from which the hydrochloride
  13. customwas precipitated
  14. customThe resulting material was recrystallized from ethyl acetate/ethanol
  15. filtrationAfter filtration
  16. washwashing with ethyl acetate and ether
  17. customthe product was air-dried

Sources & evidence

ORD record
ord-6c3a6c8bef354cd391cb8ffcfa8fe451
Source dataset
uspto-grants-1985_06
Patent number
US04521537

Reaction notes

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