Triethylamine → 6-Chloro-2-[[4-(3-chloro4-methoxyphenyl)-1-piperazinyl]-methyl]imidazo[1,2-a]pyridine

HRID 1416295Notes

Reaction equation

HRID 1416295 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:13][C:14]1[CH:15]=[C:16]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].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:16]4[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([Cl:13])[CH:15]=4)[CH2:27][CH2:26]3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 47395621-(3-Chloro-4-methoxyphenyl)piperazineHCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine3×

Product 1

HCID 193671516-Chloro-2-[[4-(3-chloro4-methoxyphenyl)-1-piperazinyl]-methyl]imidazo[1,2-a]pyridineYield 62%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (Example 4, Step 1; 0.290 g), 1-(3-chloro-4-methoxyphenyl)piperazine (0.271 g), triethylamine (Aldrich; 0.159 g), and ethylene glycol (2 mL) is stirred at 80° C. for 40 min, at which time another 0.031 g of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine is added; after another 45 min, an additional 0.025 g of 6-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine is added. When the mixture has stirred for a total of 2 h, it is cooled and partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel using methanol/dichloromethane (2/98) to give 0.29 g of the title compound after crystallization from ethyl acetate/hexane; mp 99-100.5 ° C.; MS m/z 390, 392; IR (mineral oil) 1510, 1501, 795, 1072, 1321 cm-1. 1H NMR (CDCl3) δ2.75, 3.14, 3.78, 3.84, 6.83, 6.97, 7.13, 7.52, 7.55, 8.14.

Workup

  1. additionis added
  2. temperatureis cooled
  3. custompartitioned between dichloromethane and aq. sodium bicarbonate
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-bbdc27d318ee48a6983a436b69eb9cb9
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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