1-((Pyridin-4-yl)methyl)piperazine → HCID 11271356, compound

HRID 967427Notes

Reaction equation

HRID 967427 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][CH:20]=1)[C:15]([OH:17])=O.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[N:43]1[CH:48]=[CH:47][C:46]([CH2:49][N:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)=[CH:45][CH:44]=1>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:53]2[CH2:54][CH2:55][N:50]([CH2:49][C:46]3[CH:45]=[CH:44][N:43]=[CH:48][CH:47]=3)[CH2:51][CH2:52]2)=[O:17])[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8087151-((Pyridin-4-yl)methyl)piperazineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22052318HCID 22052318, compound

Product 1

HCID 11271356HCID 11271356, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.100 g (0.321 mmol) of 3-[2-(2,4-Dichlorophenyl)-ethoxy]-benzoic acid was dissolved in 2 ml of DMF and treated with 0.148 g (1.28 mmol) of N-NEM and 0.105 g (0.321 mmol) of TOTU and 0.0569 g (0.32 mmol) of 1-Pyridin-4-ylmethyl-piperazine. 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-2b3581be3b0f4b3fb86dc2d0a4496469
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

Loading…