Triethylamine → HCID 19367111, compound

HRID 1416280Notes

Reaction equation

HRID 1416280 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.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=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:26]3[CH2:25][CH2:24][N:23]([C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([O:16][CH3:15])[CH:18]=4)[CH2:28][CH2:27]3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 814291-(3-Methoxyphenyl)piperazine dihydrochlorideHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 19367111HCID 19367111, compoundYield 72.7%

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; 0.409 g), 1-(3-methoxyphenyl)piperazine dihydrochloride (Aldrich; 0.450 g), triethylamine (Aldrich; 0.686 g), and ethylene glycol (2 mL) give 0.440 g of the title compound after chromatography (silica gel, methanol/dichloromethane, 4/96) and crystallization from dichloromethane/ethyl ether/hexane; mp 132-133.5° C.; MS m/z 356; IR (mineral oil) 805, 2817, 1198, 1171, 1580, 1502 cm-1. 1H NMR (CDCl3) δ2.74, 3.24, 3.78, 6.41, 6.46, 6.55, 7.11-7.19, 7.52, 7.56, 8.14.

Sources & evidence

ORD record
ord-caac999cdb5c427cb219179fa47cd15d
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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