4-Toluenesulfonyl chloride → HCID 89500606, compound

HRID 2178518Notes

Reaction equation

HRID 2178518 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:23].[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl.CN(C1C=CC=CN=1)C>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=[O:23])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 895002661-[2-(2-Hydroxyethyl)phenyl]piperidin-2-one

Product 1

HCID 89500606HCID 89500606, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dimethylaminopyridine (1.83 g, 15 mmol, 0.05 eq) and triethylamine (63.5 ml, 450 mmol, 1.5 eq) are added to a solution of 1-[2-(2-hydroxyethyl)phenyl]piperidin-2-one a2-2 (65.7 g, 300 mmol, 1 eq) in dichloromethane (250 ml) at 0° C. The mixture is stirred at 0° C. for 15 minutes, then a solution of 4-toluenesulfonyl chloride (63 g, 330 mmol, 1.1 eq) in dichloromethane (250 ml) is added dropwise. The reaction mixture is then warmed up to room temperature and stirred overnight. The reaction mixture is washed with water, 1N HCl, then dried over MgSO4, filtered and evaporated under vacuum. The residue is purified by chromatography over silicagel (gradient: CH2Cl2/MeOH from 100/0 to 98/2) to afford 99 g of 2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl 4-methylbenzenesulfonate a2-3.

Workup

  1. temperatureThe reaction mixture is then warmed up to room temperature
  2. stirringstirred overnight
  3. washThe reaction mixture is washed with water, 1N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue is purified by chromatography over silicagel (gradient: CH2Cl2/MeOH from 100/0 to 98/2)

Sources & evidence

ORD record
ord-da7465ea43c54a2eb6e5d451daa1eb5d
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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