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

HRID 1178805Notes

Reaction equation

HRID 1178805 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.[N:14]1([C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:29]=2[N:28]=[CH:27][CH:26]=[CH:25]3)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH2:10][CH2:11][N:17]3[CH2:18][CH2:19][N:14]([C:20]4[CH:21]=[CH:22][CH:23]=[C:24]5[C:29]=4[N:28]=[CH:27][CH:26]=[CH:25]5)[CH2:15][CH2:16]3)[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 118307868-(1-piperazinyl)QuinolineHCID 236144395-Chloro-3-(2-iodoethyl)-1-benzofuran

Product 1

HCID 113038978-{4-[2-(5-Chloro-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-(5-chloro-1-benzofuran-3-yl)ethyl iodide (305 mg. 1 mmol) (obtained by the above mentioned process) and 8-piperazino quinoline (213 mg, 1 mmol) was heated at 120° C. in DMSO in the presence of N,N-diisopropylethylamine (5 ml, excess) for 24 hrs. Afterwards, the reaction mixture was quenched with water and extracted with chloroform. The organic layer was washed with water and dried over anhydrous MgSO4 and concentrated to dryness. The dark colored solid was purified by silica-gel column chromatography by initially eluting it with 70% ethyl acetate:hexane and then with 5% methanol:ethyl acetate. 8-{4-[2-(5-chloro-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline was isolated as a yellow oil. Yield: 120 mg (30%); (M+H): 392; 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, 8H); 3.51˜2.50 (m, 12H).

Workup

  1. customobtained by the
  2. customAfterwards, the reaction mixture was quenched with water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated to dryness
  7. customThe dark colored solid was purified by silica-gel column chromatography
  8. washby initially eluting it with 70% ethyl acetate

Sources & evidence

ORD record
ord-076c4382b5014ee38a2057f223bbdeeb
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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