Diisopropylethylamine → 2-[[4-(2,4-Dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine

HRID 849500ノート

反応式

HRID 849500 の反応式
Cl[CH2:2][C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][N:6]2[CH:12]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[N:21]1[CH2:22][CH2:23][N:24]([CH2:2][C:3]2[N:4]=[C:5]3[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][N:6]3[CH:12]=2)[CH2:25][CH2:26]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27375271-(2,4-Dichlorophenyl)piperazineHCID 32549992-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine

生成物 1

HCID 193671482-[[4-(2,4-Dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

A mixture of 2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine (Example 54, Step 1; 0.294 g), 1-(2,4-dichlorophenyl)piperazine (Example 31, Step 1; 0.396 g) diisopropylethylamine (0.35 mL), and THF (2 mL) is heated at 75° C. for 5 hours. The mixture is then concentrated under reduced pressure, partitioned between saturated aq. sodium bicarbonate and dichloromethane, and the combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) and the appropriate fractions are combined and concentrated to give 2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine. The maleic acid is formed by adding maleic acid (0.101 g) to the product dissolved in dichloromethane/methanol. Crystallization from dichloromethane/ether gives 0.2192 g of the title compound; mp 151-152° C.; MS m/z 374, 376; IR (mineral oil) 1482, 1345, 1570, 1357, 867 cm-1 ; 1H NMR (CDCl3) δ 2.61, 2.80, 3.09, 3.85, 6.67, 6.95, 7.18, 7.35, 7.56, 7.95.

後処理

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. custompartitioned between saturated aq. sodium bicarbonate and dichloromethane
  3. dry with materialthe combined organic layers are dried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d56a8ad27d9440c58376abb1dcbd5af4
出典データセット
uspto-grants-2000_01
特許番号
US06013654

反応ノート

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