Hydrochloric Acid → 2,6-dimethyl-3-piperidin-4-yl-3H-imidazo[4,5-c]pyridine

HRID 1716603Notes

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]=1

Participants

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, 0.0735 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 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 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-9156f7693b684510afab1fd0d5f13729
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803816B2

Reaction notes

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