Hydrochloric Acid → 1-(3-Hydroxypropyl)piperazin-2-one

HRID 1785141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785141
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]1=[O:25])(C(C)(C)C)(C)C.Cl>O1CCOCC1>[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][C:13]1=[O:25]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68881505HCID 68881505, Verbindung

Produkt 1

HCID 450885731-(3-Hydroxypropyl)piperazin-2-oneAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

Tert-butyl 4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-3-oxopiperazine-1-carboxylate (2.90 g, 7.8 mmol) in 1,4-dioxane (10 ml) was treated at room temperature with a 4N solution of HCl in 1,4-dioxane (15 ml) and the resulting solution stirred 4 hr then evaporated. The residue was taken up in a 10% methanol in dichloromethane solution (30 ml) and basified with a 7N solution of ammonia in methanol then filtered and the filtrate evaporated. The residue was purified by column chromatography on silica using increasing concentrations of methanolic ammonia in dichloromethane as eluent to give 1-(3-hydroxypropyl)piperazin-2-one (708 mg, 57%) as a colourless oil; NMR Soectrum:(CDCl3) 1.77 (quintet, 2H), 2.72 (s(br), 2H), 3.09 (t, 2H), 3.32 (t, 2H), 3.55 (m, 6H).

Aufarbeitung

  1. customthen evaporated
  2. filtrationthen filtered
  3. customthe filtrate evaporated
  4. customThe residue was purified by column chromatography on silica using
  5. temperatureincreasing concentrations of methanolic ammonia in dichloromethane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-e1c1357707e24276ad6d34ac35b6ba18
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504408B2

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