Potassium Carbonate → HCID 86599629, compound

HRID 748508Notes

Reaction equation

HRID 748508 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N+:3]=1[O-:10].[CH3:11][N:12]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N+:3]([O-:10])=[CH:4][C:5]([CH2:8][N:15]2[CH2:16][CH2:17][CH2:18][N:12]([CH3:11])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2283491-MethylhomopiperazineHCID 124874662-Chloro-5-chloromethylpyridine 1-oxide

Product 1

HCID 86599629HCID 86599629, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine 1-oxide (940 mg, 5.28 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333) in acetonitrile (30 mL) were added N-methylhomopiperazine (1.21 g, 10.6 mmol), and K2CO3 (730 mg, 5.28 mmol). The reaction mixture was stirred at room temperature for 3.5 days. The solvent was removed in vacuo, and the residue was partitioned between brine and ethyl acetate. The aqueous layer was extracted with another two portions of ethyl acetate and one portion of tetrahydrofuran. The combined organic layers were dried (Na2SO4), and evaporated to give 0.86 g (64% yield) of the title compound as an orange oil: 1H NMR (aceton-d6, 400 MHz) δ 8.30 (dd, J=2 Hz, 1 H), 7.60 (d, J=8 Hz, 1 H), 7.29 (dd, J=8, 2 Hz, 1 H), 3.65 (s, 2 H), 2.74-2.69 (m, 4 H), 2.62-2.54 (m, 4 H), 2.29 (s, 3 H), 1.81-1.75 (m, 2 H); MS (ES) m/z 256 (M++1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between brine and ethyl acetate
  3. extractionThe aqueous layer was extracted with another two portions of ethyl acetate and one portion of tetrahydrofuran
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-7addc23fe206429f8dd12c7c46416692
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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