Pyrrolidine → HCID 85873136, compound

HRID 748507Notes

Reaction equation

HRID 748507 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N+:3]=1[O-:10].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][N+:3]=1[O-:10]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 124874662-Chloro-5-chloromethylpyridine 1-oxide

Product 1

HCID 85873136HCID 85873136, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine 1-oxide (477 mg, 2.68 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333) in acetonitrile (10 mL) was added pyrrolidine (381 mg, 5.36 mmol), and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was dissolved in 2 M HCl(aq) and washed with ethyl acetate. The aqueous layer was alkalized to pH 8 with NaHCO3 (s), and the mixture was extracted four times with ethyl acetate. The combined organic layers were dried (Na2SO4), and the solvent was evaporated to give 0.43 g (75% yield) of the title compound as a red oil: 1H NMR (CDCl3, 400 MHz) δ 8.37 (d, J=1 Hz, 1 H), 7.44 (d, J=8 Hz, 1 H), 7.23 (dd, J=8, 2 Hz, 1 H), 3.57 (s, 2 H), 2.51 (m, 4 H), 1.80 (m, 4 H); 13C NMR (CDCl3, 100 MHz) δ 140.1, 139.9, 137.2, 126.4, 126.4, 56.4, 54.0, 23.5; MS (ES) m/z 213 (M++1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 2 M HCl(aq)
  3. washwashed with ethyl acetate
  4. extractionthe mixture was extracted four times with ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7756d94bdc524fdcbf2bdf1223006505
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

Loading…