Triethylamine → ethyl 6-[N'-(3-chlorophenyl)-N-piperazinyl]hexanoate

HRID 444668

Reaktionsgleichung

Reaktionsgleichung von HRID 444668
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 256811-(3-Chlorophenyl)piperazine monohydrochlorideHCID 117544Ethyl 6-bromohexanoate

Produkt 1

HCID 67128506ethyl 6-[N'-(3-chlorophenyl)-N-piperazinyl]hexanoateAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-chlorophenyl)piperazine hydrochloride (12 g, 0.051 mol) in anhydrous toluene (250 ml) was added triethylamine (TEA) (15.6 ml, 0.112 mol) and ethyl 6-bromohexanoate (13.6 g, 0.061 mol) and the mixture heated at reflux for 4 hours. The mixture was then cooled to room temperature, washed with water (2×100 ml), brine (100 ml), dried over Na2SO4, filtered and concentrated to dryness. The residue obtained was purified by flash chromatography on silica gel using ethyl acetate/hexane (1/1) to give ethyl 6-[N′-(3-chlorophenyl)-N-piperazinyl]hexanoate (10.3 g) as a clear oil.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 hours
  3. washwashed with water (2×100 ml), brine (100 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue obtained
  8. customwas purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0dcef08f389c4c03a153929326d5e18b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476029B2

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