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

HRID 1178806Notes

Reaction equation

HRID 1178806 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.[Cl: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]([Cl: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 236144395-Chloro-3-(2-iodoethyl)-1-benzofuranHCID 592048546-Chloro-8-(piperazin-1-yl)quinoline

Product 1

HCID 114871228-{4-[2-(5-Chloro-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-chloro-quinoline

Procedure

8-{4-[2-(5-chloro-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-chloro-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-chloro-8-piperazino quinoline (247 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: 110 mg (25%); (M+H): 427; 1HNMR (400 MHz, CDCl3):δ 8.86˜8.85 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 8.03˜8.01 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 7.57˜7.10 (m, 7H); 3.51˜2.50 (m, 12H).

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-3bf8299795044dbf8bd63d014ca516bc
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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