Triethylamine → 6-Bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine

HRID 1416265

반응식

HRID 1416265 반응식
[Br: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>[Br: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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 116228946-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridineHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

생성물 1

HCID 193671286-Bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 6-bromo-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 15, Step 1; 0.3042 g), 1-(4-chlorophenyl)piperazine dihydrochloride (Aldrich; 0.3708 g), triethylamine (Aldrich; 0.55 mL), and ethylene glycol (5.6 mL) is stirred for 1 h at 80° C. After cooling, the mixture is partitioned between water and dichloromethane. The combined organic layers are washed with brine, dried with MgSO4, and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) to give, after crystallization from ethyl acetate/methanol/dichlormetane, 0.1756 g of the title compound; mp 154-155° C.; MS m/z 404, 406, 408; IR (mineral oil) 1495, 1500, 1224, 823, 812 cm-1 ; 1H NMR (CDCl3) δ2.72, 3.19, 3.76, 6.83, 7.20, 7.22, 7.47, 7.52, 8.24.

후처리

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between water and dichloromethane
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. customto give
  8. customafter crystallization from ethyl acetate/methanol/dichlormetane, 0.1756 g of the title compound

출처 및 근거

ORD 기록
ord-94e86b75667d4d1f9cf7e59f8190eb74
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912246

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