6-Methyl-8-(piperazin-1-yl)quinoline → 8-{4-[2-(5-Chloro-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-methyl-quinoline

HRID 1178807Notes

Reaction equation

HRID 1178807 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10][CH2:11]I)[C:6]=2[CH:13]=1.[CH3:14][C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10][CH2:11][N:28]3[CH2:29][CH2:30][N:25]([C:23]4[CH:24]=[C:15]([CH3:14])[CH:16]=[C:17]5[C:22]=4[N:21]=[CH:20][CH:19]=[CH:18]5)[CH2:26][CH2:27]3)[C:6]=2[CH:13]=1

Participants

3

Reactant 2

HCID 207011566-Methyl-8-(piperazin-1-yl)quinolineHCID 236144395-Chloro-3-(2-iodoethyl)-1-benzofuran

Product 1

HCID 112582548-{4-[2-(5-Chloro-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-methyl-quinoline

Procedure

8-{4-[2-(5-chloro-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-methyl-quinoline was prepared by generally following the procedure outlined in example 12, step 6, starting from the 2-(5-chloro-1-benzofuran-3-yl)ethyl iodide (306 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: 140 mg (34%); (M+H): 406; 1HNMR (400 MHz, CDCl3): δ□8.82˜8.80 (dd, J1=1.7 Hz, J2=1.7 Hz, 1H), 8.03˜7.80 (dd, J1=1.7 Hz, J2=1.7 Hz 1H), 7.60˜6.70 (m, 7H), 3.48˜2.81 (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
  3. customhexane and then with 5% methanol:ethyl acetate, yielding a brown oil

Sources & evidence

ORD record
ord-c0f63718626a40899d5c9392306e41f9
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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