4-Iodobenzenesulfonyl chloride → HCID 17798575, compound

HRID 1840606Notes

Reaction equation

HRID 1840606 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]3=[O:20])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.[I:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>C1COCC1>[I:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH:10]3[CH2:11][CH2:12][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:8][CH2:9]3)[C:15](=[O:20])[CH2:16]2)(=[O:41])=[O:40])=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 73994-Iodobenzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 10858694HCID 10858694, compound

Product 1

HCID 17798575HCID 17798575, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1-[1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone (549 mg), sodium bicarbonate solution (5 ml), ethyl acetate (10 ml) and THF (5 ml) was added dropwise, under ice-cooling, a solution of 4-iodobenzenesulfonyl chloride (1.21 g) in THF (10 ml), and the mixture was stirred at 0° C. for 1 hour. The separated organic layer was washed with saturated brine, dried (MgSO4) and concentrated, and the residue was purified with silica gel column chromatography (acetone:methanol=9: 1→1:1) and washed with water to give colorless crystals of 4-(4-iodobenzenesulfonyl)-1-[1-(4-pyridyl)-4-piperidylmethyl]-2-piperazinone (155 mg). A part of the crystals were treated with hydrochloric acid to give colorless crystals of the title compound as hydrochloride.

Workup

  1. additionwas added dropwise, under ice-
  2. temperaturecooling
  3. washThe separated organic layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified with silica gel column chromatography (acetone:methanol=9: 1→1:1)
  7. washwashed with water

Sources & evidence

ORD record
ord-377ce02f7af6418583f23e466342c138
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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