Ethanol → Ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate

HRID 1459459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1459459
C(O)C.Cl.[NH2:5][OH:6].[C:7]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1)#[N:8].C[O-].[Na+]>O>[NH2:8][C:7](=[N:5][OH:6])[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 4060541Ethyl 4-cyanopiperidine-1-carboxylateHCID 10942334Sodium Methoxide

Produkt 1

HCID 54150879Ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethanol (150 ml) was added to a solution of hydroxylamine hydrochloride (17.25 g) in water (48 ml). Ethyl 4-cyano-1-piperidinecarboxylate (45 g) was added and the mixture was cooled. Sodium methoxide (44.4 g) was added dropwise at RT and the reaction mixture was stirred for 30 minutes at 60° C. The reaction mixture was cooled, filtered and the filtrate evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5). The pure fractions were collected and the solvent evaporated, yielding 25 g (40%) of ethyl 4-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate. This fraction was redissolved in 2-propanone and converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 22 g (35%) of ethyl 4-[amino(hydroxyimino)methyl]-1-piperidine-carboxylate hydrochloride (intermediate 2).

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customThe residue was purified by column chromatography on silica gel (eluent: CH2Cl2 /CH3OH 95/5)
  6. customThe pure fractions were collected
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-09199164904446ca90d349309dcc1eb3
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05854261

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