Piperidine → Piperidine, 1-[2-(ethylsulfonyl)ethyl]-

HRID 2226470Notes

Reaction equation

HRID 2226470 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7]Cl)(=[O:5])=[O:4])[CH3:2].[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+]>>[CH2:1]([S:3]([CH2:6][CH2:7][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 101406Ethane, 1-chloro-2-(ethylsulfonyl)-

Product 1

HCID 3104333Piperidine, 1-[2-(ethylsulfonyl)ethyl]-Yield 82.7%

Procedure

Mix 2-chloroethyl ethyl sulfone (1.2 g, 7.66 mmol) and piperidine (2 mL, 20 mmol). Stir at room temperature for 2 hours. Treat with 5N sodium hydroxide, extract with ethyl acetate (3×50 mL) and dry (MgSO4). Concentrate in vacuo to yield 1.3 g yellow oil which crystallizes. Purify by silica gel chromatography (ethyl acetate) to yield 550 mg (35%) of the title compound as a clear oil which crystallizes; mp 45°-47° C.

Workup

  1. extractionextract with ethyl acetate (3×50 mL)
  2. dry with materialdry (MgSO4)
  3. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-979d9525aacd48d9906aa36270522784
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

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