Acetone → HCID 23513835, compound

HRID 353542Notes

Reaction equation

HRID 353542 reaction equation
Cl.[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5].[CH2:25](I)[CH3:26].C(=O)([O-])[O-].[K+].[K+].[CH3:34][C:35](C)=O>>[CH2:2]([O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][CH2:19][N:18]([CH2:34][CH3:35])[CH2:17]2)(=[O:14])=[O:15])=[CH:9][CH:8]=1)[C:3]#[C:4][CH3:5]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69726584HCID 69726584, compound

Product 1

HCID 23513835HCID 23513835, compound

Procedure

3-{[4-(2-Butynyloxy)phenyl]sulfonyl}-3-piperidinecarboxylate hydrogen chloride (2.97 g, 8.0 mmol), ethyl iodide (1.28 g, 8 mmol) and dry powdered potassium carbonate (3.8 g) in dry acetone (60 ml) was heated to reflux for 18 hours. The mixture was allowed to cool and the potassium salts were filtered and concentrated. The residue was extracted with chloroform and washed with H2O, dried over sodium sulfate and concentrated to afford ethyl 3-{[4-(2-butynyloxy)phenyl]sulfonyl}-1-ethyl-3-piperidinecarboxylate. This product was used without further purification. Amber gum, yield 3.47 g (99%/0); MS (ES): m/z 394 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. temperatureto cool
  4. filtrationthe potassium salts were filtered
  5. concentrationconcentrated
  6. extractionThe residue was extracted with chloroform
  7. washwashed with H2O
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4309376cf7044a43b5bb6f9635ee1526
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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