Piperidine → HCID 20505900, compound

HRID 1703715Notes

Reaction equation

HRID 1703715 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([Cl:15])[C:3]=1[C:4]([OH:6])=[O:5].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:13])=[O:12])=[C:7]([Cl:15])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 35382162,6-dichloro-3-chlorosulfonyl-benzoic Acid

Product 1

HCID 20505900HCID 20505900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dichloro-5-chlorosulfonylbenzoic acid (960 mg.; 3.3 m moles) is added portion-wise to 1.95 g. (0.0165 mole) of piperidine in 15 ml. of dry methylene chloride, and the mixture heated to reflux for 1.5 hrs. Th solvent and excess amine are removed under reduced pressure and the residue dissolved in 15 ml. of 2N sodium hydroxide. The aqueous base solution is extracted (2 × 50 ml.) with ether and acidified with 6N hydrochloric acid. The precipitated gum is filtered, dried and allowed to crystallize in hexane, 1.1 g., m.p. 145°-150° C. A small sample is recrystallized from acetonitrile, m.p. 142°-145° C.

Workup

  1. temperatureto reflux for 1.5 hrs
  2. customTh solvent and excess amine are removed under reduced pressure
  3. dissolutionthe residue dissolved in 15 ml
  4. extractionThe aqueous base solution is extracted (2 × 50 ml.) with ether
  5. filtrationThe precipitated gum is filtered
  6. customdried
  7. customto crystallize in hexane
  8. customA small sample is recrystallized from acetonitrile, m.p. 142°-145° C.

Sources & evidence

ORD record
ord-e09f772a1f4f4aa7bab578b19991ce58
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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