1-Phenylpiperazine → HCID 57682692, compound

HRID 494253Notes

Reaction equation

HRID 494253 reaction equation
[C:1](OC(OC(OC(C)(C)C)=O)=O)(OC(C)(C)C)=[O:2].[NH2:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1.C(F)(F)(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.[C:79]1([N:85]2[CH2:90][CH2:89][NH:88][CH2:87][CH2:86]2)[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1>C(Cl)Cl>[C:79]1([N:85]2[CH2:90][CH2:89][N:88]([C:1]([NH:19][C:20]3[CH:29]=[C:28]4[C:23]([CH:24]=[CH:25][CH:26]=[N:27]4)=[CH:22][CH:21]=3)=[O:2])[CH2:87][CH2:86]2)[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 113777-AminoquinolineHCID 67646Fluorocarbon FC 70HCID 11780301diBoc-carbonate

Product 1

HCID 57682692HCID 57682692, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of di-tert-butyl tricarbonate (60 mg, 0.23 mmol) in DCM (1 ml) was added in one portion, a solution of 7-aminoquinoline (D55) (30 mg, 0.21 mmol) in DCM (1 ml). After 5 mins, when gas evolution was complete, tris -amine resin (12 mg 0.04 mmol) was added, then after 1 h a solution of 4-phenylpiperazine (32 ul, 0.21 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was then purified directly by SPE column chromatography, eluting with an EtOAc/60-80° C.-petroleum ether gradient, followed by treatment with excess methyl isocyanate resin to remove unreacted 7-aminoquinoline starting material from the product. On completion the resin was removed by filtration and filtrate concentrated in vacuo to give the title compound as an orange gum. 1H NMR (250 MHz, CDCl3) δ (ppm): 8.85 (dd, 1H), 8.09 (dd, 1H), 7.93 (dd, 1H), 7.82 (s, 1H), 7.76 (d, 1H), 7.30 (m, 3H), 6.94 (m, 3H), 6.83 (br, 1H), 3.72 (m, 4H), 3.28 (m, 4H).

Workup

  1. customThe reaction mixture was then purified directly by SPE column chromatography
  2. washeluting with an EtOAc/60-80° C.-petroleum ether gradient
  3. customto remove unreacted 7-aminoquinoline starting material from the product
  4. customOn completion the resin was removed by filtration and filtrate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e53c10e6c4b40d3ba3a9925b371c1af
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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