1-((Pyridin-4-yl)methyl)piperazine → {3-[2-(2,4-Dichlorophenyl)-Ethoxy]-4-Methyl-Phenyl}-(4-Pyridin-4-Ylmethyl-Piperazin-1-Yl)-Methanone

HRID 967422Notes

Reaction equation

HRID 967422 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]=[CH:19][C:20]=1[CH3:21])[C:15]([OH:17])=O.[N:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:24][CH:23]=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:32]2[CH2:33][CH2:34][N:29]([CH2:28][C:25]3[CH:24]=[CH:23][N:22]=[CH:27][CH:26]=3)[CH2:30][CH2:31]2)=[O:17])[CH:18]=[CH:19][C:20]=1[CH3:21]

Participants

5

Reactant 3

HCID 8087151-((Pyridin-4-yl)methyl)piperazineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 220523883-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methyl-benzoic acid

Product 1

HCID 22052331{3-[2-(2,4-Dichlorophenyl)-Ethoxy]-4-Methyl-Phenyl}-(4-Pyridin-4-Ylmethyl-Piperazin-1-Yl)-Methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.094 g (0.29 mmol) of 3-[2-(2,4-dichloro-phenyl)-ethoxy]-4-methyl-benzoic acid was dissolved in 2 ml of DMF and treated with 0.146 ml (1.16 mmol) of N-NEM and 51 mg (0.29 mmol) of 1-Pyridin-4-ylmethyl-piperazine and 0.098 g (0.3 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 DCM and the solution was washed three times with saturated aqueous sodium bicarbonate. The organic phase was dried with sodium sulphate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with DCM, and DCM/MeOH (20/1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe solution was washed three times with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic phase was dried with sodium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with DCM, and DCM/MeOH (20/1)

Sources & evidence

ORD record
ord-ccf29c314190483b9c4eeed6c7991a41
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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