1-(1-Naphthyl)piperazine → 6-[2-(4-Naphthalen-1-yl-piperazin-1-yl)-ethyl]-3H-benzooxazol-2-one

HRID 1639265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639265
[C:1]1([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:18][CH2:19][C:20]1[CH:29]=[CH:28][C:23]2[NH:24][C:25](=[O:27])[O:26][C:22]=2[CH:21]=1.C(N(CC)CC)C.[I-].[Na+]>C(O)C>[C:1]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]3[CH:29]=[CH:28][C:23]4[NH:24][C:25](=[O:27])[O:26][C:22]=4[CH:21]=3)[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 13421-(1-Naphthyl)piperazineHCID 5238Sodium IodideHCID 8471TriethylamineHCID 133060876-Bromoethylbenzoxazolone

Produkt 1

HCID 98208876-[2-(4-Naphthalen-1-yl-piperazin-1-yl)-ethyl]-3H-benzooxazol-2-oneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a 100 ml round-bottomed flask equipped with magnetic stirrer, condenser, and nitrogen inlet were added 0.618 g (2.10 mmol) of N-(1-naphthyl)piperazine, 0.472 g (1.95 mmol) of 6-(2-bromoethyl)-benzoxazolone, 0.411 ml (2.92 mmol) of triethylamine, 50 ml ethanol, and a catalytic amount of sodium iodide. The reaction was refluxed for 3 days, cooled, and evaporated to a brown gum. The gum was partitioned between 50 ml water and 75 ml methylene chloride, the pH adjusted with aqueous 1N NaOH solution, and a little methanol added to facilitate phase separation. The methylene chloride layer was dried over sodium sulfate and evaporated, then chromatographed on silica gel. Fractions containing the product were combined and evaporated, the residue taken up in ethyl acetate, treated with hydrochloride gas, and the resulting hydrochloride salt of the product filtered off to give the white solid title compound, m.p. 282°-285° C., 213 mg (23% yield).

Aufarbeitung

  1. customTo a 100 ml round-bottomed flask equipped with magnetic stirrer, condenser, and nitrogen inlet
  2. temperatureThe reaction was refluxed for 3 days
  3. temperaturecooled
  4. customevaporated to a brown gum
  5. customThe gum was partitioned between 50 ml water and 75 ml methylene chloride
  6. additiona little methanol added
  7. customphase separation
  8. dry with materialThe methylene chloride layer was dried over sodium sulfate
  9. customevaporated
  10. customchromatographed on silica gel
  11. additionFractions containing the product
  12. customevaporated
  13. additiontreated with hydrochloride gas
  14. filtrationthe resulting hydrochloride salt of the product filtered off

Quellen und Nachweise

ORD-Eintrag
ord-806f2bc35a9440379f5bde723d562e91
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04883795

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