Dimethylformamide → 1-Tosylpiperidin-4-one

HRID 270758Notes

Reaction equation

HRID 270758 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) 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-77dad1a0bf934584ae410fe4693578d3
Source dataset
uspto-grants-2008_11
Patent number
US07449595B2

Reaction notes

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