Sodium hydride → 1-(2-Propynyl)-4-(2-pyridinyl)-piperazine

HRID 1448480

Reaktionsgleichung

Reaktionsgleichung von HRID 1448480
[C:1](Br)#[C:2][CH3:3].[Na].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[H-].[Na+]>O.CN(C)C=O>[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:13][CH2:14][N:15]([CH2:3][C:2]#[CH:1])[CH2:16][CH2:17]1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 944591-(2-Pyridyl)piperazine2×HCID 1372791-Propyne, 1-bromo-HCID 5360545Sodium

Produkt 1

HCID 106319131-(2-Propynyl)-4-(2-pyridinyl)-piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Propynylbromide (11.9 g.) was added to the sodium salt of N-(2-pyridyl)piperazine prepared from 16.3 g. of N-(2-pyridyl)piperazine and 4.8 g. of sodium hydride/50% mineral oil dispersion in 50 ml. of dry dimethylformamide. The mixture was stirred at 50° C. for 3 hours and then carefully poured into 3 volumes of cold water. This mixture was extracted with several portions of either and the combined ether extracts were washed twice with 10% aqueous hydrochloric acid. The acidic extract was made strongly alkaline by adding 40% aqueous sodium hydroxide under cooling. The mixture was then extracted several times with ether and the combined extracts were dried over magnesium sulfate. The latter was then removed by filtration, and the filtrate was evaporated to produce a brown oil. Distillation under reduced pressure gave N'-(2-pyridyl)-N-(2-propynyl)piperazine, b.p. 153°-4° C./3.5 mm, as a yellow oil which showed the expected NMR and IR spectra.

Aufarbeitung

  1. customprepared from 16.3 g
  2. extractionThis mixture was extracted with several portions of either and the combined ether extracts
  3. washwere washed twice with 10% aqueous hydrochloric acid
  4. extractionThe acidic extract
  5. additionby adding 40% aqueous sodium hydroxide
  6. temperatureunder cooling
  7. extractionThe mixture was then extracted several times with ether
  8. dry with materialthe combined extracts were dried over magnesium sulfate
  9. customThe latter was then removed by filtration
  10. customthe filtrate was evaporated
  11. customto produce a brown oil
  12. distillationDistillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55aaf42d1f144f55894ab88aad3aa39c
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04180574

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