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

HRID 2206

反応式

HRID 2206 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-9af742574ebf4d4aa094524fbbb466cc
出典データセット
uspto-grants-1998_03
特許番号
US05728701

関連ノート

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