Hydrochloric Acid → Piperidine, 1-[(2,5-dichlorophenyl)sulfonyl]-

HRID 483871Notes

Reaction equation

HRID 483871 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I-].[Na+].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[S:30](Cl)(=[O:32])=[O:31].[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.Cl>CN1CCCC1=O.C(O)C.[Ni](Cl)Cl.[Zn]>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1[S:30]([N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)(=[O:32])=[O:31]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 8082PiperidineHCID 11776TriphenylphosphineHCID 794012,5-Dichlorobenzenesulfonyl chloride

Product 1

HCID 646492Piperidine, 1-[(2,5-dichlorophenyl)sulfonyl]-

Reagents, catalysts & solvents 4

HCID 23994ZincCatalyst2×HCID 24385Nickel DichlorideCatalystHCID 702EthanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
50 °C

Procedure

Anhydrous nickel(II) chloride (60 mg, 0.46 mmole), triphenylphosphine (800 mg, 3.05 mmole), sodium iodide (180 mg, 1.2 mmole), and activated zinc powder (1.2 g, 18 mmole) are placed into a 25 ml flask under an inert atmosphere along with 7 ml of anhydrous N-methylpyrrolidinone (NMP). This mixture is stirred at 50° C. for about 10 minutes, leading to a deep-red coloration. A solution of 3.4 g (11.6 mmole) of 2,5-dichlorobenzenesulfonylpiperidine, which is prepared by the reaction of 2,5-dichlorobenzenesulfonyl chloride with piperidine, in 8 ml of anhydrous NMP is then added by syringe. After stirring for about 60 hours, the resulting highly viscous solution is poured into 200 ml of 1 molar hydrochloric acid in ethanol to dissolve the excess zinc metal and to precipitate the polymer. This suspension is filtered and triturated with acetone to afford, after isolation and drying, solid polyparabenzenesulfonylpiperidine.

Workup

  1. additionis then added by syringe
  2. stirringAfter stirring for about 60 hours
  3. customto precipitate the polymer
  4. filtrationThis suspension is filtered
  5. customtriturated with acetone
  6. customto afford
  7. customafter isolation and drying

Sources & evidence

ORD record
ord-61eece08728c4c67967e1f823177ee36
Source dataset
uspto-grants-1993_07
Patent number
US05227457

Reaction notes

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