Potassium Carbonate → 3-(2-Morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine

HRID 1783785Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[N:1]1([CH2:7][CH2:8][C:9]2[N:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]3=[CH:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-morpholin-4-yl-N-pyridin-2-ylmethyl-propionamide (5.4 g, 21.7 mmol) in 1,2-dichloroethane (100 mL), cooled in an ice bath, was added POCl3 (12 mL). The mixture was heated to 80° C. for 3 h. After this time the mixture was allowed to cool and poured slowly into 10% aqueous potassium carbonate (500 mL). The mixture was extracted with dichloromethane (200 mL) and ethyl acetate (200 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica to yield 3-(2-morpholin-4-yl-ethyl)-imidazo[1,5-a]pyridine (3.89, 78%).

Workup

temperatureto cool
extractionThe mixture was extracted with dichloromethane (200 mL) and ethyl acetate (200 mL)
dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica

Sources & evidence

ORD record: ord-b4303cc0898b432ea7c687346ea67b50
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501438B2

Reaction notes

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