Hydrochloric Acid → 2,6-dimethyl-3-piperidin-4-yl-3H-imidazo[4,5-c]pyridine
Reaction equation
[CH3:1][C:2]1[N:11]([CH:12]2[CH2:17][CH2:16][N:15](C(=O)C)[CH2:14][CH2:13]2)[C:5]2[CH:6]=[N:7][C:8]([CH3:10])=[CH:9][C:4]=2[N:3]=1.Cl>C(O)C>[CH3:1][C:2]1[N:11]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:5]2[CH:6]=[N:7][C:8]([CH3:10])=[CH:9][C:4]=2[N:3]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
A solution of 1-[4-(2,6-dimethyl-imidazo[4,5-c]-pyridin-3-yl)-piperidin-1-yl]-ethanone (20 mg, 0.074 mmol) in ethanol (0.5 mL) was treated with concentrated HCl (0.5 mL). The reaction mixture was heated at 100° C. for 18 h. The solvent was evaporated and the mixture was diluted with water (2 mL). The mixture was washed twice with diethyl ether and the aqueous phase was adjusted to pH=10 by addition of a solution of 25% aqueous NaOH. The aqueous mixture was extracted with CH2Cl2 (5×10 mL). The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 2,6-dimethyl-3-piperidin-4-yl-3H-imidazo[4,5-c]pyridine (13 mg, 77%) as a light yellow solid which was used without further purification.
Workup
- customThe solvent was evaporated
- additionthe mixture was diluted with water (2 mL)
- washThe mixture was washed twice with diethyl ether
- additionthe aqueous phase was adjusted to pH=10 by addition of a solution of 25% aqueous NaOH
- extractionThe aqueous mixture was extracted with CH2Cl2 (5×10 mL)
- washThe combined extracts were washed with brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-39de3414425e4b7d8efb8dbeb0830324
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803816B2
Reaction notes
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