Potassium Carbonate → 4-Amino-1-N-Cbz-piperidine

HRID 1078

Reaktionsgleichung

Reaktionsgleichung von HRID 1078
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2C(=O)C3=CC=CC=C3C2=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.C([O-])([O-])=O.[K+].[K+]>C(O)C.[Cl-].[Na+].O>[NH2:17][CH:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 21831105Phenylmethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-piperidinecarboxylate

Produkt 1

HCID 178466404-Amino-1-N-Cbz-piperidineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-Benzyloxycarbonyl-4-phthalimidylpiperidine (1.50 g, 4.27 mmol), prepared in Example 16B, was taken up in 20 mL of ethanol. To this solution was added hydrazine monohydrate (35 mL, 700 mmol) and this mixture was heated at 100° C. for 3 h. Brine solution (40 mL) and 10% aq. K2CO3 (60 mL) were added and the mixture was extracted with 5% MeOH/CHCl3 (3×). The combined extracts were washed with 2N aq. HCl, 2N aq. NaOH, brine solution, dried over Na2SO4 and concentrated to give 0.847 g, (85%) of 4-amino-1-benzyloxycarbonylpiperidine. [1H]-NMR(CDCl3) consistent with structure.

Aufarbeitung

  1. extractionthe mixture was extracted with 5% MeOH/CHCl3 (3×)
  2. washThe combined extracts were washed with 2N aq. HCl, 2N aq. NaOH, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2cac9a20d7c04458add12877e56c0bdb
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723490

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