Hydrochloric Acid → HCID 70156360, compound

HRID 1249729Notes

Reaction equation

HRID 1249729 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[C:29]([CH3:31])[N:28]=[C:27]([CH3:32])[N:26]=4)[CH2:21][CH2:20]3)=O)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:30]=[C:29]([CH3:31])[N:28]=[C:27]([CH3:32])[N:26]=4)[CH2:23][CH2:24]3)[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18328907HCID 18328907, compound

Product 1

HCID 70156360HCID 70156360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(4-Chlorophenylsulphonyl)-4-[1-(2,6-dimethylpyrimidin-4-yl)-4-piperidylcarbonyl]piperazine (603 mg, 0.96 mol) was refluxed in THF (5 ml), borane-dimethyl sulphide complex was added continuously and reflux continued for 4 hours. Reaction was stirred over a weekend to a residue. THF (5 ml) was added followed by 0.2 μL 6M HCl and stirred for 6 hours. Reaction basified by addition of dilute NaOH and partitioned between DCM and H2O. Organic layer was sepearted and dried in vacuo affording a white solid. Further purification by filtration column chromatography (silica) DCM to 10% MeOH/DCM and concentration of relevant fractions afforded 1-(4-chlorophenylsulphonyl)-4-[1-(2,6-dimethylpyrimidin-4-yl)-4-piperidylmethyl]piperazine a white solid/foam, 0.39 g (80%), mp73-74° C.;

Workup

  1. additionborane-dimethyl sulphide complex was added continuously
  2. temperaturereflux
  3. customReaction
  4. stirringstirred for 6 hours
  5. customReaction
  6. custompartitioned between DCM and H2O
  7. customdried in vacuo
  8. customaffording a white solid
  9. customFurther purification
  10. filtrationby filtration column chromatography (silica) DCM to 10% MeOH/DCM and concentration of relevant fractions

Sources & evidence

ORD record
ord-d1d2bc56c16d4ef9874fa146923a3633
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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