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

HRID 1703713Notes

Reaction equation

HRID 1703713 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 reflux for 1.5 hrs. The solvent is removed under reduced pressure, and the residue is partitioned between 25 ml. of 1N sodium hydroxide solution and diethyl ether. The aqueous layer is separated, acidified with 6N hydrochloric acid and 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. temperatureto reflux for 1.5 hrs
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is partitioned between 25 ml
  4. customThe aqueous layer is separated
  5. customthe resulting precipitated product
  6. filtrationfiltered
  7. customdried
  8. customRecrystallization from acetonitrile
  9. customgave the purified product, m.p. 244°-245° C.

Sources & evidence

ORD record
ord-3870e7b5ddfc45428a8349bae4114d75
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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