Dimethylformamide → HCID 86650192, compound

HRID 2093078Notes

Reaction equation

HRID 2093078 reaction equation
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1>>[Cl:3][C:24]1[CH2:25][CH2:26][N:21]([S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:11])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[CH2:22][C:23]=1[CH:9]=[O:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 5609571-Tosylpiperidin-4-one

Product 1

HCID 86650192HCID 86650192, compound

Procedure

A solution of POCl3 (1.5 eq.) in DMF (2.5 eq) at 0° C. was stirred for 15 min. 1-[(4-methylphenyl) sulfonyl]piperidin-4-one (1.0 eq) obtained from step I was added to the above solution and the reaction was continued at room temperature for 2 h Reaction was quenched with water and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired 4-chloro-1-[(4-methylphenyl)sulfonyl]-1,2,5,6-tetrahydropyridine-3-carbaldehyde.

Workup

  1. customReaction
  2. customwas quenched with water
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product, which
  7. customon purification by column chromatography

Sources & evidence

ORD record
ord-4591df65d0f14b8dbded9e7dd5bc188c
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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