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

HRID 1416302ノート

反応式

HRID 1416302 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.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(N(C(C)C)CC)(C)C>CN(C=O)C.C1COCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][C:3]3[N:4]=[C:5]4[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][N:6]4[CH:12]=3)[CH2:24][CH2:23]2)=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 32549992-(Chloromethyl)-8-methylimidazo[1,2-a]pyridineHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

生成物 1

HCID 193671342-[[4-(4-Chlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine収率 41.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒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-α]pyridine (0.297 g), 1-(4-chlorophenyl) piperazine dihydrochloride (Aldrich; 0.534 g), triethylamine (0.8 mL), THF (6 mL), and DMF (2 mL) is heated at 75° C. for 4 hours. Diisopropylethylamine (0.3 mL) is added and the mixture is stirred another hour, at which time the mixture is concentrated under reduced pressure and the residue is partitioned between saturated aq. sodium bicarbonate and dichloromethane. The organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96). The appropriate fractions are combined and concentrated and the residue is crystallized from ethyl acetate/hexane to give 0.231 g of the title compound; mp 102-104° C.; MS m/z 340; IR (mineral oil) 1495, 1338, 2819, 1227, 743 cm-1 ; 1H NMR (CDCl3) δ2.61, 2.78, 3.22, 3.85, 6.68, 6.82, 6.94, 7.18, 7.58, 7.95.

後処理

  1. concentrationis concentrated under reduced pressure
  2. customthe residue is partitioned between saturated aq. sodium bicarbonate and dichloromethane
  3. dry with materialThe organic layers are dried with MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on silica gel
  6. concentrationconcentrated
  7. customthe residue is crystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-8d41bfd6a2974ba583652b53f48474de
出典データセット
uspto-grants-1999_06
特許番号
US05912246

反応ノート

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