Chloride → 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-[(E)-2-chloroethenyl]benzenesulfonyl]-2-piperazinone

HRID 1840598Notes

Reaction equation

HRID 1840598 reaction equation
[Cl-].[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH2:18][C:17]2=[O:33])[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[CH:34](Cl)(Cl)[Cl:35].C(OCC)(=O)C>C1COCC1>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[CH:26]=[CH:27][C:28](/[CH:31]=[CH:34]/[Cl:35])=[CH:29][CH:30]=3)(=[O:24])=[O:23])[CH2:18][C:17]2=[O:33])[CH2:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:5]

Participants

6

Reactant 4

HCID 312ChlorideHCID 6212ChloroformHCID 8857Ethyl AcetateHCID 177986001-[1-(Tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone

Product 1

HCID 865866061-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-[(E)-2-chloroethenyl]benzenesulfonyl]-2-piperazinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of chromiun (II) chloride (737 mg) in THF (10 ml) was added a solution of 1-[1-(tert-butoxycarbonyl)-4-piperidylmethyl]-4-[4-formylbenzenesulfonyl]-2-piperazinone (466 mg) and chloroform (0.160 ml) in THF (7 ml), and the mixture was refluxed for 1 hour. To the reaction solution was added ethyl acetate, and the mixture was washed with water and saturated brine, dried and concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give colorless crystals of the title compound (235 m g).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. washthe mixture was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-fd17a1dd014f4d79852326f5bc888cb9
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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