1-((Pyridin-4-yl)methyl)piperazine → HCID 11785872, compound

HRID 1831759Notes

Reaction equation

HRID 1831759 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[C:15]([OH:17])=O.[N:25]1[CH:30]=[CH:29][C:28]([CH2:31][N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)=[CH:27][CH:26]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:15]([N:35]2[CH2:36][CH2:37][N:32]([CH2:31][C:28]3[CH:27]=[CH:26][N:25]=[CH:30][CH:29]=3)[CH2:33][CH2:34]2)=[O:17])[CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 8087151-((Pyridin-4-yl)methyl)piperazineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22052346HCID 22052346, compound

Product 1

HCID 11785872HCID 11785872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.100 g (0.269 mmol) of 3-[2-(2,4-Dichlorophenyl)-ethoxy]-4,5-dimethoxy-benzoic acid was dissolved in 2 ml of DMF and treated with 0.124 g (1.08 mmol) of N-NEM and 0.0477 g (0.27 mmol) of 1-Pyridin-4-ylmethyl-piperazine and 0.088 g (0.269 mmol) of TOTU. The solution was stirred for 16 h at RT. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and the solution was washed twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with a gradient of 0–17% MeOH in DCM.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe solution was washed twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride
  3. dry with materialThe organic phase was dried with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with a gradient of 0–17% MeOH in DCM

Sources & evidence

ORD record
ord-6f14c7c7fed648ae9251a9821e308103
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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