Sodium Bicarbonate → 4-(+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-1-(4-imidazol-1-ylphenyl)piperazine

HRID 1987757Notes

Reaction equation

HRID 1987757 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:18][C:19]1([CH:34]=O)[CH2:23][CH:22]2[CH:24]([CH3:33])[C:25]([N+:30]([O-:32])=[O:31])=[C:26]([CH3:29])[C:27]([CH3:28])=[C:21]2[O:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)(=O)C.O>[N+:30]([C:25]1[CH:24]([CH3:33])[CH:22]2[CH2:23][C:19]([CH2:18][N:15]3[CH2:16][CH2:17][N:12]([C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[CH:4][N:3]=[CH:2]5)=[CH:11][CH:10]=4)[CH2:13][CH2:14]3)([CH3:34])[O:20][C:21]2=[C:27]([CH3:28])[C:26]=1[CH3:29])([O-:32])=[O:31]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231182901-(4-(1H-imidazol-1-yl)phenyl)piperazineHCID 866073542,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-aldehyde

Product 1

HCID 866088044-(+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-1-(4-imidazol-1-ylphenyl)piperazineYield 100.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.7 g of 1-(4-imidazol-1-ylphenyl)-piperazine and 0.7 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-aldehyde were dissolved in 20 ml of methylene chloride and 1 ml of acetic acid as a catalyst was added, followed by stirring at room temperature for 30 minutes. To the resulting reaction solution, 1.2 g of sodium triacetoxyborohydride was added, followed by stirring at room temperature for 30 minutes. After the completion of the reaction, the reaction solution was poured into water, neutralized with an aqueous saturated sodium hydrogen carbonate solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, 1.3 g of the objective product was obtained.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 30 minutes
  3. customAfter the completion of the reaction
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing magnesium sulfate
  8. filtrationby filtration
  9. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-01284d3bf21943e8ab4e9fc58f50db17
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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