1,4-Diiodobutane → HCID 18430942, Verbindung

HRID 1278623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1278623
C([N-]C(C)C)(C)C.[Li+].[CH2:9]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(P(N(C)C)(N(C)C)=O)C.[I:41][CH2:42][CH2:43][CH2:44][CH2:45]I>O1CCCC1>[CH2:9]([N:16]1[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH:24]([CH2:45][CH2:44][CH2:43][CH2:42][I:41])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20][CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 123371,4-DiiodobutaneHCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 18430976Ethyl 4-(phenylmethyl)-1-piperazinebutanoate

Produkt 1

HCID 18430942HCID 18430942, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

To a stirred solution of lithium diisopropylamide (2 M, 32.0 ml, 6.36 mmol) in tetrahydrofuran (420 ml) was added ethyl 4-(4-benzyl-1-piperazinyl)-butanoate (6.47 g, 21.2 mmol) (Preparation 1) at −78° C. and the mixture was stirred for 1 h at the same temperature. To this mixture was added HMPA (19.4 ml) and the resultant mixture was added to a solution of 1,4-diiodobutane (13.2 g, 4.25 mmol) in tetrahydrofuran (22 ml) at −78° C. After 1 h, the temperature was raised to −50° C. and the mixture was stirred for 1 hour. The reaction was quenched by adding AcOH (0.230 ml). After the mixture was basified with aq. saturated NaHCO3, then the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 200-350 mesh/500 g/hexane:ethyl acetate=2:1) to provide a yellow oil (6.3 g/63%).

Aufarbeitung

  1. waitAfter 1 h
  2. stirringthe mixture was stirred for 1 hour
  3. customThe reaction was quenched
  4. additionby adding AcOH (0.230 ml)
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/500 g/hexane:ethyl acetate=2:1)
  11. customto provide a yellow oil (6.3 g/63%)

Quellen und Nachweise

ORD-Eintrag
ord-2f22f2a192634bd4a625a038efe32f5b
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06444677B2

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