Acetone → HCID 23513835, compound

HRID 278323Notes

Reaction equation

HRID 278323 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%); 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-dd051cc541b3438c97c876251a083e4f
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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