1-(4-Pyridyl)piperazine → iso-Propyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

HRID 2219

반응식

HRID 2219 반응식
Br[CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:8]([O:9][CH2:10][C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1>C(#N)C>[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([CH2:2][C:3]([C:5]3[CH:18]=[CH:17][C:8]([O:9][CH2:10][C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:29][CH2:30]2)=[CH:21][CH:20]=1

참가 물질

4

반응물 2

HCID 705171-(4-Pyridyl)piperazineHCID 20315599HCID 20315599, 화합물

생성물 1

HCID 54144385iso-Propyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxyacetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

iso-Propyl 4-bromoacetylphenoxyacetate (6.3 g) was added to a stirred, cooled (4° C.) solution of 1-(4-pyridyl)piperazine (6.5 g) in acetonitrile (225 ml). Stirring was continued for 1 hour at 4° C., then overnight at ambient temperature when the precipitated solid was removed. The filtrate was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. Purification by flash chromatography on silica, eluting firstly with 0 to 10% v/v methanol/dichloromethane and then toluene/ethyl acetate/.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid. Recrystallisation from iso-propanol gave the title compound, 2.1 g: m.p. 121°-122° C.; NMR (d6DMSO) δ 8.14 (2H, d), 7.98 (2H, d), 7.02 (2H, d), 6.80 (2H, d), 4.99 (1H, m), 4.85 (2H, s), 3.84 (2H, s), 3.33 (4H, t), 2.62 (4H, t), 1.22 (6H, d); m/e 398 (M+H)+ ; calculated for C22H27N3O4 : C, 66.5; H, 6.9; N, 10.6. found: C, 65.8; H, 6.8; N, 10.4%.

후처리

  1. customovernight at ambient temperature when the precipitated solid was removed
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customPurification by flash chromatography on silica
  7. washeluting firstly with 0 to 10% v/v methanol/dichloromethane
  8. customtoluene/ethyl acetate/.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid
  9. customRecrystallisation from iso-propanol

출처 및 근거

ORD 기록
ord-c0b95ca8088a4d46af3551fafa170fb2
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728701

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