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

HRID 1178818Notes

Reaction equation

HRID 1178818 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[C:8]([CH2:11][CH2:12]I)[C:7]=2[CH:14]=1.[N:15]1([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[CH:28][CH:27]=[CH:26]3)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[C:8]([CH2:11][CH2:12][N:18]3[CH2:19][CH2:20][N:15]([C:21]4[CH:22]=[CH:23][CH:24]=[C:25]5[C:30]=4[N:29]=[CH:28][CH:27]=[CH:26]5)[CH2:16][CH2:17]3)[C:7]=2[CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 118307868-(1-piperazinyl)QuinolineHCID 236144423-(2-Iodoethyl)-5-methoxy-1-benzofuran

Product 1

HCID 114520258-{4-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-(5-methoxy-1-benzofuran-3-yl)ethyl iodide (301 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. At the end, 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 eluting it initially with 70% ethyl acetae:hexane and then with 5% methanol:ethyl acetate. 8-{4-[2-(5-methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline was isolated as brown solid. mp 78° C.; Yield: 120 mg (31%); (M+H): 388; 1HNMR (400 MHz, CDCl3): δ 8.90˜8.88 (dd, J1=1.7 Hz, J2=1.7 Hz,, 1H); 8.13˜8.10 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 7.51˜6.88 (m, 8H); 3.68 (s, 3H); 3.68˜2.82 (m, 12H).

Workup

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

Sources & evidence

ORD record
ord-5bc230fc29b24ebab5f68e40a9b560bb
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

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