1,1'-Carbonyldiimidazole → 2-Oxo-3-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-c]pyridine

HRID 1453935Notes

Reaction equation

HRID 1453935 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12](CC2C=CC=CC=2)[CH2:11][CH2:10]1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>O1CCCC1>[O:23]=[C:22]1[N:8]([CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 222932454-Amino-3-[(1-benzylpiperidin-4-yl)amino)pyridine

Product 1

HCID 222931682-Oxo-3-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-c]pyridineYield 129.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-amino-3-[(1-benzylpiperidin-4-yl)amino)pyridine (2.8 g, 9.9 mmol) and carbonyldiimidazole (3.0 g, 18.5 mmol) in tetrahydrofuran (100 mL) was refluxed overnight. The reaction was cooled, concentrated and partitioned between chloroform (500 mL) and saturated sodium carbonate (100 mL). The organic phase was dried over magnesium sulfate and concentrated to give the title compound (2.8 g). MS 209 (M+1).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. custompartitioned between chloroform (500 mL) and saturated sodium carbonate (100 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63acbfffda914b29998310485e526553
Source dataset
uspto-grants-2009_01
Patent number
US07476665B2

Reaction notes

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