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

HRID 1703713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1703713
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-3870e7b5ddfc45428a8349bae4114d75
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04124590

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