Hydrazine hydrate (1:1) → tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylate

HRID 1978341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978341
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]3[C:20](=O)[NH:19]C(=O)C3(CCC)C=CC=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:20][NH2:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 219936813-(1-Tert-butoxycarbonyl-4-piperidyl)-1-propylphthalimide

Produkt 1

HCID 22990164tert-Butyl 4-(3-aminopropyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 20.24 g (54.34 mM) of 3-(1-tert-butoxycarbonyl-4-piperidyl)-1-propylphthalimide in 350 ml of ethanol was added 7.9 ml (163 mM) of hydrazine monohydrate and the mixture was refluxed for one hour. After cooling to room temperature, the resulting precipitate (phthalide) was filtered off and washed with a small amount of ethanol. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The residue was extracted with chloroform and the organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure to provide the title compound. Light-yellow oil. Yield 13.08 g (99%)

Aufarbeitung

  1. temperaturethe mixture was refluxed for one hour
  2. filtrationthe resulting precipitate (phthalide) was filtered off
  3. washwashed with a small amount of ethanol
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionThe residue was extracted with chloroform
  6. washthe organic layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over MgSO4
  8. distillationThe solvent was then distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e54714cc4c9846cd8831f3ea4ed0d582
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235731B1

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