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Hydrochloric Acid → 4-Benzamido-1-(4-phenyl-4-hydroxybutyl)piperidine

HRID 437241
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 437241
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.[OH-].[Na+]>[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[OH:20])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 100892541-(3-Benzoylpropyl)-4-benzamidopiperidine

Produkt 1

HCID 214305654-Benzamido-1-(4-phenyl-4-hydroxybutyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 14798
Sodium Hydroxide
Lösungsmittel

Versuchsvorschrift

4-Benzamido-(4-phenyl-4-oxobutyl)piperidine (3.4 g.) was dissolved in methanol (125 ml.) and a solution of sodium borohydride (6.0 g.) in 0.2 N sodium hydroxide (30 ml.) was added at room temperature over a period of 0.5 hours. The resulting mixture was stirred for a further 2 hours and then heated under reflux for 4 hours. The resulting mixture was filtered, the filtrate evaporated almost to dryness and then treated with water (100 ml.). The colourless solid was filtered off, washed with water, dried, dissolved in a small amount of ethanolic hydrogen chloride and treated with ether until crystallisation commenced. Filtration and drying gave 1.875 g. of the hydrochloride of the title compound, m.p. 221° C. (Found: C, 68.1; H, 7.4; N, 7.3. C22H28N2O2.HCl requires C, 67.9; H, 7.5; N, 7.2%).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe resulting mixture was filtered
  4. customthe filtrate evaporated almost to dryness
  5. additiontreated with water (100 ml.)
  6. filtrationThe colourless solid was filtered off
  7. washwashed with water
  8. customdried
  9. dissolutiondissolved in a small amount of ethanolic hydrogen chloride
  10. additiontreated with ether until crystallisation
  11. filtrationFiltration
  12. customdrying
  13. customgave 1.875 g

Quellen und Nachweise

ORD-Eintrag
ord-297fba93c64e4981b7fc2b43e36094e7
Quelldatensatz
uspto-grants-1977_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04029801

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