1-Methylpiperazine → HCID 178481024, compound

HRID 1784963Notes

Reaction equation

HRID 1784963 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9](Cl)(Cl)Cl)=[N:8][C:4]=2[CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C([O-])(=O)C.[NH4+:26]>C(#N)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9](=[NH:26])[N:19]3[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 517165Ammonium AcetateHCID 178477904HCID 178477904, compound

Product 1

HCID 178481024HCID 178481024, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of 5-chloro-2-trichloromethyl-1H-benzoimidazole (100 mg, 0.37 mmol) in acetonitrile (4 mL) was added N-methylpiperazine (0.04 mL, 0.4 mmol). The mixture was stirred for 10 min then ammonium acetate (29 mg, 0.38 mmol) was added. After 18 h the reaction mixture was diluted with satd aq NaHCO3 (10 mL), and then extracted with dichloromethane (3×10 mL). The combined extracts were dried (Na2SO4) and then concentrated under reduced pressure. The crude product was purified on silica gel (10 g; 0-10% methanol (2 M NH3)/dichloromethane) to afford 23 mg (22%) of the title compound. MS (ESI): mass calculated for C13H16N4O, 277.11; m/z found, 278.2 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.79-7.74 (m, 2H)1 7.45 (dd, J=8.6, 2.0 Hz, 1H), 4.23-4.17 (m, 4H), 3.63-3.58 (m, 4H), 3.01 (s, 3H).

Workup

  1. extractionextracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified on silica gel (10 g; 0-10% methanol (2 M NH3)/dichloromethane)

Sources & evidence

ORD record
ord-684e4a3330224d4e9dccb562656e8dbc
Source dataset
uspto-grants-2009_03
Patent number
US07504426B2

Reaction notes

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