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

HRID 1290485Notes

Reaction equation

HRID 1290485 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 firom 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%.

Workup

  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 firom ethyl acetate/hexane

Sources & evidence

ORD record
ord-f7621c992956442ca94474c45b112160
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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