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Hydrochloric Acid → 1-Benzyl-4-(3,4-dihydro-2,2-dioxo-2,1,3-benzothiadiazin-1-yl)-piperidine monohydrochloride

HRID 2166900
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2166900
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][NH2:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:23](=[N-])(=[O:25])=[O:24].N1C=CC=CC=1.[ClH:33]>C(O)C.C(OCC)(=O)C>[ClH:33].[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH2:21][NH:22][S:23]2(=[O:25])=[O:24])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 13051023N-[2-(Aminomethyl)phenyl]-1-benzylpiperidin-4-amineHCID 18672990Sulfurylamide

Produkt 1

HCID 134171231-Benzyl-4-(3,4-dihydro-2,2-dioxo-2,1,3-benzothiadiazin-1-yl)-piperidine monohydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In this reference example, 33.0 g (112.4 m.mols) of 1-benzyl-4-[N-(o-aminomethylphenyl)-amino]-piperidine, 21.6 g (224.8 m.mols) of sulfuryl amide and 250 ml of pyridine are mixed and refluxed with heating for 8 hours. The reaction solution is cooled to room temperature, concentrated to 70 ml and poured into 500 ml of ice water. The mixture is mixed with 300 ml of chloroform, stirred and adjusted to pH 9 with 2 N aqueous sodium hydroxide. The chloroform layer is separated with separating funnel and the remaining water layer is further extracted with chloroform (300 ml×3). The chloroform layers are combined, washed with water (300 ml×4), dried and concentrated to obtain an oily residue. This residue is dissolved in 150 ml of ethanol. To the solution, 50 ml of 5.7 N hydrogen chloride in ethyl acetate is added. The resultant solution is concentrated under reduced pressure. The crystalline residue is mixed with 50 ml of ethanol and filtered to obtain 29.0 g of the desired product. This compound is tested for NMR after it has been freed from hydrochloric acid, and it is tested for IR in its unaltered form of hydrochloride.

Aufarbeitung

  1. temperaturerefluxed
  2. temperaturewith heating for 8 hours
  3. concentrationconcentrated to 70 ml
  4. additionpoured into 500 ml of ice water
  5. additionThe mixture is mixed with 300 ml of chloroform
  6. customThe chloroform layer is separated
  7. customwith separating funnel
  8. extractionthe remaining water layer is further extracted with chloroform (300 ml×3)
  9. washwashed with water (300 ml×4)
  10. customdried
  11. concentrationconcentrated
  12. customto obtain an oily residue
  13. concentrationThe resultant solution is concentrated under reduced pressure
  14. additionThe crystalline residue is mixed with 50 ml of ethanol
  15. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-603638f218d94d749537586f41ec8f9e
Quelldatensatz
uspto-grants-1983_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04390536

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