1-((Pyridin-4-yl)methyl)piperazine → 1-({3-[2-(2,4-Dichlorophenyl)ethoxy]-4-methoxyphenyl}carbonyl)-4-(pyridin-4-ylmethyl)piperazine

HRID 1831754Notes

Reaction equation

HRID 1831754 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[O:21][CH3:22])[C:15]([OH:17])=O.[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=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:33]2[CH2:34][CH2:35][N:30]([CH2:29][C:26]3[CH:25]=[CH:24][N:23]=[CH:28][CH:27]=3)[CH2:31][CH2:32]2)=[O:17])[CH:18]=[CH:19][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 154803323-[2-(2,4-Dichlorophenyl)ethoxy]-4-methoxybenzoic acid

Product 1

HCID 101853721-({3-[2-(2,4-Dichlorophenyl)ethoxy]-4-methoxyphenyl}carbonyl)-4-(pyridin-4-ylmethyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.100 g (0.29 mmol) of 3-[2-(2,4-Dichloro-phenyl)-ethoxy]-4-methoxy-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 1 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 n-heptane/ethyl acetate (1/1), ethyl acetate, and ethyl acetate/MeOH (10/1).

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 n-heptane/ethyl acetate (1/1), ethyl acetate, and ethyl acetate/MeOH (10/1)

Sources & evidence

ORD record
ord-38d6d4893508477aa189da098d92eeff
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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