1,1'-Carbonyldiimidazole → 2-oxo-3-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-c]pyridine

HRID 20076

Reaction equation

HRID 20076 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]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:11][CH2:10]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 222931702-oxo-3-(1-benzylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-c]pyridineYield 91.7%

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-bdc6e64c37f3441a80847c866a4ea28c
Source dataset
uspto-grants-2010_06
Patent number
US07745427B2

Linked notes

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