rel-(3R,5S)-3,5-Dimethylpiperidine → 2,3-Dichloro-5-(cis-3,5-dimethylpiperidinosulfonyl)benzoic Acid

HRID 1730601Notes

Reaction equation

HRID 1730601 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[Cl:9][C:10]1[C:18]([Cl:19])=[CH:17][C:16]([S:20](Cl)(=[O:22])=[O:21])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>C(Cl)Cl>[Cl:9][C:10]1[C:18]([Cl:19])=[CH:17][C:16]([S:20]([N:4]2[CH2:5][C@H:6]([CH3:8])[CH2:7][C@H:2]([CH3:1])[CH2:3]2)(=[O:22])=[O:21])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 641101rel-(3R,5S)-3,5-DimethylpiperidineHCID 205061302,3-Dichloro-5-(chlorosulfonyl)benzoic acid

Product 1

HCID 536984792,3-Dichloro-5-(cis-3,5-dimethylpiperidinosulfonyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To cis-3,5-dimethylpiperidine (374 mg.; 3.3 m moles) in 3 ml. of methylene chloride is added 192 mg. (0.66 m moles) of 2,3-dichloro-5-chlorosulfonylbenzoic acid and the mixture heated to refluxfor 1.5 hrs. The solvent is removed under reduced pressure, and the residueis partitioned between 25 ml. of 1N sodium hydroxide solution and diethyl ether. The aqueous layer is separated, acidified with 6N hydrochloric acidand the resulting precipitated product filtered and dried, 230 mg., m.p. 235°-238° C. Recrystallization from acetonitrile gave the purified product, m.p. 244°-245° C.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residueis partitioned between 25 ml
  3. customThe aqueous layer is separated
  4. customthe resulting precipitated product
  5. filtrationfiltered
  6. customdried
  7. customRecrystallization from acetonitrile
  8. customgave the purified product, m.p. 244°-245° C.

Sources & evidence

ORD record
ord-ad060d491d7f4f7ca74db3fe6d62c2e2
Source dataset
uspto-grants-1976_11
Patent number
US03992441

Reaction notes

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