Triethylamine → 2-[[4-(2,4-Dichlorophenyl)-1-piperazinyl]methyl]-6-ethoxyimidazo[1,2-a]pyridine

HRID 1416282Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][N:6]2[CH:14]=1.[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C>C1COCC1>[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N:23]1[CH2:24][CH2:25][N:26]([CH2:2][C:3]2[N:4]=[C:5]3[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[CH:7][N:6]3[CH:14]=2)[CH2:27][CH2:28]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-(chloromethyl)-6-ethoxyimidazo[1,2-α]pyridine (0.204 g), 1-(2,4-dichlorophenyl) piperazine (Example 31, Step 1; 0.2283 g), triethylamine (Aldrich; 0.15 mL), and THF (1.3 mL) is stirred at 75° C. until the reaction is judged complete by thin layer chromatography. The cooled mixture is concentrated under reduced pressure and partitioned between dichloromethane and saturated aq. sodium bicarbonate. The combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (2/98) and crystallized from ethyl acetate/ether to give 0.0936 g of the title compound; mp 171-172° C.; MS m/z 404, 406; IR (mineral oil) 1478, 1189, 797, 1508, 1273 cm-1 ; 1H NMR (CDCl3) δ1.45, 2.77, 3.08, 3.77, 3.98, 6.94, 7.17, 7.34, 7.45, 7.47, 7.60.

Workup

concentrationThe cooled mixture is concentrated under reduced pressure
custompartitioned between dichloromethane and saturated aq. sodium bicarbonate
dry with materialThe combined organic layers are dried with MgSO4
concentrationconcentrated under reduced pressure
customThe residue is chromatographed on silica gel
customcrystallized from ethyl acetate/ether

Sources & evidence

ORD record: ord-f2043ab59cee4c0daf56667af82e41e3
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912246

Reaction notes

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