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

HRID 1291864Notes

Reaction equation

HRID 1291864 reaction equation
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

Participants

4

Reactant 2

HCID 705171-(4-Pyridyl)piperazineHCID 20315599Isopropyl 4-(bromoacetyl)phenoxyacetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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/0.880 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%.

Workup

  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/0.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid
  9. customRecrystallisation from iso-propanol

Sources & evidence

ORD record
ord-db717d8789094dc198efe4665417648f
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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