Triethylamine → HCID 19367144, compound

HRID 1416257Notes

Reaction equation

HRID 1416257 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.Cl.Cl.[Cl:15][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.C(N(CC)CC)C>C(O)CO>[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]([Cl:15])=[CH:21][CH:20]=4)[CH2:27][CH2:26]3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridineHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

Product 1

HCID 19367144HCID 19367144, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Following the general procedure of Example 11 and making noncritical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 4, Step 1; 0.354 g), 1-(4-chlorophenyl)piperazine dihydrochloride (Aldrich; 0.475 g), triethylamine (0.552 g), and ethylene glycol (2 mL) give 0.363 g of the title compound after chromatography (silica gel, methanol/dichloromethane, 4/96) and crystallization from dichloromethane/hexane; mp 145-146° C.; MS m/z 360; IR (mineral oil) 823, 1500, 1496, 1225, 814 cm-1. 1H NMR (CDCl3) δ2.72, 3.19, 3.76, 6.83, 7.13, 7.19, 7.52, 7.53, 8.14.

Sources & evidence

ORD record
ord-4afe1f52826345c5a6efad3d90f3043e
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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