1,1'-Carbonyldiimidazole → HCID 9793874, compound

HRID 2296624Notes

Reaction equation

HRID 2296624 reaction equation
[N:1](=[C:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1)[OH:2].[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11]>C(Cl)Cl>[N:1]1[O:2][C:10](=[O:11])[N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:3]=12

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178526316HCID 178526316, compound

Product 1

HCID 9793874HCID 9793874, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 2 g (16 mmol) of 2-hydroximinohomopiperidine (Maybridge) in 20 mL of methylene chloride (CH2Cl2) was added 2.5 g (16 mmol) of 1,1′-carbonyldiimidazole (CDI). This was stirred at 25° C. for six days. This solution was diluted with CH2Cl2, washed with water, dried (MgSO4), filtered and concentrated to afford 2.2 g (89% yield) of the title compound as a white semi-solid. Mass Spectra for C7H10N2O2: M+H155. 1H NMR,(CDCl3) d 1.5-1.9 (m, 6H), 2.6 (dd, 2H), 3.6 (dd, 2H). 13C NMR (CDCl3) d 25.3, 26.0, 28.2, 30.2, 43.7, 159.1, 161.6.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d3799136a80544978ccef5dd941db22b
Source dataset
uspto-grants-2002_12
Patent number
US06489323B1

Reaction notes

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