6-Methyl-8-(piperazin-1-yl)quinoline → 8-{4-[2-(6-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-methyl-quinoline

HRID 1178800Notes

Reaction equation

HRID 1178800 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7]([CH2:10][CH2:11]I)=[CH:8][O:9][C:5]=2[CH:4]=1.[CH3:15][C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH:25]=1)[N:22]=[CH:21][CH:20]=[CH:19]2>>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7]([CH2:10][CH2:11][N:29]3[CH2:30][CH2:31][N:26]([C:24]4[CH:25]=[C:16]([CH3:15])[CH:17]=[C:18]5[C:23]=4[N:22]=[CH:21][CH:20]=[CH:19]5)[CH2:27][CH2:28]3)=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 207011566-Methyl-8-(piperazin-1-yl)quinolineHCID 236144453-(2-Iodoethyl)-6-methoxy-1-benzofuran

Product 1

HCID 113616238-{4-[2-(6-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-methyl-quinoline

Procedure

8-{4-[2-(6-methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-methyl-quinoline was prepared by generally following the procedure outlined in example 9, step 6, starting from the step of 2-(6-methoxy-1-benzofuran-3-yl)ethyl iodide (301 mg, 1 mmol) and 6-methyl-8-piperazino quinoline (227 mg, 1 mmol). The product was purified by silica-gel column chromatography by initially eluting it with 80% ethyl acetate:hexane and then with 5% methanol:ethyl acetate, yielding a brown oil Yield: 210 mg (52%); (M+H): 402; 1HNMR (400 MHz, CDCl3):δ 8.81˜8.80 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 8.02˜7.99 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H) 7.46˜6.88 (m, 7H); 3.9 (s, 3H); 3.60˜2.82 (m, 12H); 2.5 (s, 3H).

Workup

  1. customThe product was purified by silica-gel column chromatography
  2. washby initially eluting it with 80% ethyl acetate

Sources & evidence

ORD record
ord-92313da60f574ad7aaf845c3dff2dc03
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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