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1-(Benzyloxycarbonyl)-4-[(4-nitrophenoxy)methyl]piperidine → 4-[(4-Aminophenoxy)methyl]-1-(benzyloxycarbonyl)piperidine

HRID 345446
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 345446
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.Cl.[Zn]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:16][CH2:15]2)=[CH:24][CH:23]=1
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Komponenten

5

Edukt 1

HCID 199924221-(Benzyloxycarbonyl)-4-[(4-nitrophenoxy)methyl]piperidine

Produkt 1

HCID 199924324-[(4-Aminophenoxy)methyl]-1-(benzyloxycarbonyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of the product of part (ii) (10.0 g) in ethanol (400 ml) and 2N hydrochloric acid (200 ml) was heated to reflux with stirring. Zinc dust (8.80 g) was added at such a rate that the ensuing reaction was not too vigorous. The mixture was heated under reflux for 0.25 hour and then cooled and filtered. The filtrate was made basic with 0.88 ammonia solution and diluted with a large volume of water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel, eluting with dichloromethane. Earlier fractions contained impurity and the pure product was eluted in the later fractions. The product fractions were combined and evaporated to give an oil, (5.50 g). The product darkened rapidly and was used directly without further purification.

Aufarbeitung

  1. temperatureto reflux
  2. customthat the ensuing reaction
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 0.25 hour
  5. temperaturecooled
  6. filtrationfiltered
  7. additiondiluted with a large volume of water
  8. extractionThe mixture was extracted several times with ethyl acetate
  9. washthe combined extracts were washed with water
  10. dry with materialdried (Na2SO4)
  11. customEvaporation of the solvent
  12. customgave an oil which
  13. customwas chromatographed on silica gel
  14. washeluting with dichloromethane
  15. washthe pure product was eluted in the later fractions
  16. customevaporated
  17. customto give an oil, (5.50 g)
  18. customwas used directly without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d975b56833114bfa8d88aa36cd6ca394
Quelldatensatz
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05057528

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