Sodium Hydroxide → 1-(Methylsulphonyl)piperidin-4-one

HRID 968708Notes

Reaction equation

HRID 968708 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH3:10][S:11](Cl)(=[O:13])=[O:12].[OH-].[Na+]>C1COCC1>[CH3:10][S:11]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 2723901Piperonylamine

Product 1

HCID 120720291-(Methylsulphonyl)piperidin-4-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
29 °C

Procedure

To a stirred solution of 4-piperidone hydrate hydrochloride (40.00 g, 0.260 mol) and THF (320 ml) was added CH3SO2Cl (31.0 ml, 0.402 mol) and 15% aq. NaOH (156 ml) such that the temperature of the reaction mixture was maintained at 26-32° C. After this addition, the reaction mixture was stirred at RT for 2 hours and transferred to a separatory funnel. The organic layer was collected and the aqueous layer was extracted with THF (2×250 ml). The combined organic layers were dried over Na2SO4. After filtration, the concentrated residue was washed with hexane to give the product (46.0 g, 100%). 1H NMR (CDCl3) δ 3.59 (t, J=6.00 Hz, 4H), 2.89 (s, 15 3H), 2.59 (t, J=5.6 Hz, 4H).

Workup

  1. additionAfter this addition
  2. customtransferred to a separatory funnel
  3. customThe organic layer was collected
  4. extractionthe aqueous layer was extracted with THF (2×250 ml)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationAfter filtration
  7. washthe concentrated residue was washed with hexane

Sources & evidence

ORD record
ord-73f2f90f7c5247029c1ccb63fac72360
Source dataset
uspto-grants-2007_12
Patent number
US07304076B2

Reaction notes

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