Triethylamine → HCID 15432352, compound

HRID 1416251Notes

Reaction equation

HRID 1416251 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N:6]2[CH:12]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(O)CO>[F:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[CH2:25][CH2:24][N:23]([CH2:2][C:3]3[N:4]=[C:5]4[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][N:6]4[CH:12]=3)[CH2:22][CH2:21]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 516892Sodium BicarbonateHCID 3345586HCID 3345586, compound

Product 1

HCID 15432352HCID 15432352, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of 2-(chloromethyl)-6-methylimidazo[1,2-a]pyridine (0.302 g), 1-(4-fluorophenyl) piperazine (Aldrich; 0.319 g), triethylamine (Aldrich; 0.26 mL), and ethylene glycol (2 mL) is stirred for 2.25 h at 80-85° C. The cooled mixture is then poured into saturated aq. sodium bicarbonate and extracted several times with dichloromethane. The combined organic layers are washed with brine, dried with MgSO4, and concentrated under reduced pressure. The crude material is chromatographed on silica gel using methanol/dichloromethane/ammonium hydroxide (4/96/0.25) and crystallized from ethyl acetate/hexane to give 0.300 g of the title compound; mp 112-112.5° C.; ms m/z 324; IR (mineral oil) 1511, 804, 1234, 1246, 1345 cm-1 ; 1H NMR (CDCl3) δ2.31, 2.74, 3.15, 3.76, 6.90, 7.46, 7.86.

Workup

  1. extractionextracted several times with dichloromethane
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material is chromatographed on silica gel
  6. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8f5f0269353e442680b06f1910ebf735
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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