Sodium hydride → Ethyl 4-[4-[4-(4-pyridyl)piperazin-1-yl]phenoxy]butyrate

HRID 2206

Reaktionsgleichung

Reaktionsgleichung von HRID 2206
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:15][CH:14]=3)[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 149869034-(4-(4-Pyridyl)piperazin-1-yl)phenol

Produkt 1

HCID 18918274Ethyl 4-[4-[4-(4-pyridyl)piperazin-1-yl]phenoxy]butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred suspension of 4-(4-(4-pyridyl)piperazin-1-yl)-phenol (1.34 g) in dry DMF (20 ml) was treated with sodium hydride (60% dispersion in mineral oil, 0.21 g) and the mixture stirred for 1 hour. To the resulting solution was added ethyl 4-bromobutyrate and the mixture was stirred for 16 hours. Solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water, filtered through phase separating paper (Whatman 1PS) and evaporated. The residue was purified by flash chromatography on silica, eluting with 1-5/92.5/6 v/v/v methanol/ethyl acetate/aqueous ammonia (SG 0.89) and recrystallised from ethyl acetate/hexane to give the title compound (0.7 g) as a solid: m.p. 84°-85° C.; NMR (CDCl3) δ 8.3(2H,d); 6.86(4H,c); 6.72(2H,d); 4.12(2H,q); 4.0(2H,t); 3.47(4H,m); 3.20(4H,m); 2.5(2H,t); 2.1(2H,m); 1.26(3H,t); m/e 370(M+H)+ ; calculated for C21H27N3O3C, 68.3; H, 7.4; N, 11.4. Found: C, 68.1; H, 7.4; N, 11.1%.

Aufarbeitung

  1. stirringthe mixture was stirred for 16 hours
  2. customSolvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water
  5. filtrationfiltered through phase
  6. customseparating paper (Whatman 1PS)
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica
  9. washeluting with 1-5/92.5/6 v/v/v methanol/ethyl acetate/aqueous ammonia (SG 0.89)
  10. customrecrystallised from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9af742574ebf4d4aa094524fbbb466cc
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728701

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