Triethylamine → 6,8-Dichloro-2-[[4-(4-fluorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine

HRID 1416260Notes

Reaction equation

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

Participants

Conditions

Temperature: 82.5 °C

Procedure

A mixture of 6,8-dichloro-2-(chloromethyl)imidazo[1,2-α]pyridine (0.3064 g), 1-(4-fluorophenyl)piperazine (Aldrich; 0.266 g), triethylamine (Aldrich; 0.21 mL), and ethylene glycol (2 mL) is stirred for 1 h at 80-85° C. After cooling, the mixture is partitioned between water and dichloromethane and the organic layers are washed with brine and dried over MgSO4. After concentration under reduced pressure, the residue is chromatographed on silica gel using methanol/dichloromethane (4/96) and the appropriate fractions are combined and concentrated and the residue is crystallized from ethyl acetate/hexane to give 0.3098 g of the title compound; mp 126.5-127.5° C.; MS m/z 378, 380; IR (mineral oil) 1510, 1215, 1335, 826, 1224 cm-1 ; 1H NMR (CDCl3) δ2.75, 3.15, 3.83, 6.87, 6.96, 7.26, 7.62, 8.09.

Workup

temperatureAfter cooling
customthe mixture is partitioned between water and dichloromethane
washthe organic layers are washed with brine
dry with materialdried over MgSO4
concentrationAfter concentration under reduced pressure
customthe residue is chromatographed on silica gel
concentrationconcentrated
customthe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-1c543c94d1de4a9c8bfd999e7477df7e
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912246

Reaction notes

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