Piperazin-4-ylacetophenone → HCID 19367137, compound

HRID 1416289Notes

Reaction equation

HRID 1416289 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[CH3:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1)=[O:15]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:25]3[CH2:24][CH2:23][N:22]([C:19]4[CH:18]=[CH:17][C:16]([C:14](=[O:15])[CH3:13])=[CH:21][CH:20]=4)[CH2:27][CH2:26]3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 97269Piperazin-4-ylacetophenoneHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 19367137HCID 19367137, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure of Example 39, Step 2, 6-chloro-2-(chloromethyl) imidazo[1,2-α]pyridine (Example 4. Step 1; 0.294 g), 4-piperazinoacetophenone (Aldrich; 0.366 g), and THF (3 mL) are converted to product, which is chromatographed on silica gel using methanol/dichlormethane (2/98), followed by crystallization from ethyl acetate/dichloromethane, to give 0.270 g of the title compound in two crops; mp 185.5-187° C.; MS m/z 368; IR (mineral oil) 1600, 1661, 1252, 1327, 1197 cm-1 ; 1H NMR (CDCl3) δ2.52, 2.72, 3.40, 3.76, 6.86, 7.13, 7.52, 7.54, 7.86, 8.15.

Workup

  1. customis chromatographed on silica gel
  2. customfollowed by crystallization from ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-e620e6ef62b541ec83164b0550638a42
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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