1,1'-Carbonyldiimidazole → HCID 19987387, compound

HRID 973948Notes

Reaction equation

HRID 973948 reaction equation
C(N[CH:4]([OH:13])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)C.[C:14](N1C=CN=C1)([N:16]1[CH:20]=[CH:19]N=C1)=[O:15]>O1CCCC1>[CH2:20]([N:16]1[CH:5]([CH2:6][C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)[CH2:4][O:13][C:14]1=[O:15])[CH3:19]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 19987362HCID 19987362, compound

Product 1

HCID 19987387HCID 19987387, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude α-(ethylamino)-4-pyridinepropanol (2.07 g, 0.0122 mol) is stirred in dry tetrahydrofuran (20 mL) with activated 3Å sieves for about 10 minutes. Carbonyldiimidazole (2.26 g, 0.0139 mol) is added and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated and Kugelrohr distilled at 80-100° C. and 2 mm Hg to remove excess imidazole. The residue is chromatographed on silica gel eluting with 10:1 chloroform:methanol to afford 1.7 g of the title compound as an amber oil.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. distillationKugelrohr distilled at 80-100° C.
  3. custom2 mm Hg to remove excess imidazole
  4. customThe residue is chromatographed on silica gel eluting with 10:1 chloroform

Sources & evidence

ORD record
ord-24846243c85842b0be00818fa55c245b
Source dataset
uspto-grants-1991_11
Patent number
US05066662

Reaction notes

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