1,1'-Carbonyldiimidazole → HCID 67095615, compound

HRID 909093Notes

Reaction equation

HRID 909093 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH3:2].[C:13](N1C=CN=C1)([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:14]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[O:14])[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

Product 1

HCID 67095615HCID 67095615, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(piperidin-4-yl)-acetic acid ethyl ester (211.4 mg, 1.234 mmol, Oakwood,) in N,N-dimethyl formamide (5.0 mL) was added 1,1′-carbonyldiimidazole (216 mg, 1.332 mmol Aldrich). After it was stirred at rt for 4 days under an argon atmosphere, the solvent was removed and the reaction mixture was extracted with EtOAc, and washed with water (2×), and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give [1-(imidazole-1-carbonyl)-piperidin-4-yl]acetic acid ethyl ester (293.3 mg, 1.10 mmol, 89.6%) which was used without further purification.

Workup

  1. customthe solvent was removed
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washwashed with water (2×), and saturated NaCl
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-90c60cda525e46ba86939b7a173994dc
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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