Dimethylformamide → 1-Tosylpiperidin-4-one

HRID 348389Notes

Reaction equation

HRID 348389 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.C(N(CC)CC)C.CN(C=O)C>C(Cl)Cl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 337214-Piperidone

Product 1

HCID 5609571-Tosylpiperidin-4-oneYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

para-Toluenesulfonyl chloride (13.8 g, 72.2 mmol) was added to a suspension of 4-piperidone (10.1 g, 65.7 mmol) and triethylamine (7.30 g, 72.2 mmol) in CH2Cl2 (100 ml). After stirring at room temperature for 2 hours DMF (50 ml) was added to the reaction mixture and the stirring was continued overnight. The reaction mixture was concentrated in vacuo and saturated aqueous sodium bicarbonate was added to the residue. The resulting precipitate which formed was collected by suction filtration. The precipitate was washed with water followed by hexane and then dried under high vacuum to afford a white solid (9.4 g) which was used without further purification. 1H NMR (300 MHz, CDCl3) δ 7.69 (d, 2H, J=8.1 Hz), 7.34 (d, 2H, J=8.1 Hz) 3.39 (m, 4H), 2.55 (m, 4H), 2.44 (s, 3H).

Workup

  1. additionwas added to the reaction mixture
  2. concentrationThe reaction mixture was concentrated in vacuo and saturated aqueous sodium bicarbonate
  3. additionwas added to the residue
  4. customThe resulting precipitate which formed
  5. filtrationwas collected by suction filtration
  6. washThe precipitate was washed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-3241b1e9d9ec48418042e1add4f5364b
Source dataset
uspto-grants-2007_02
Patent number
US07176238B1

Reaction notes

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