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

HRID 1178799Notes

Reaction equation

HRID 1178799 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.[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:14]=[CH:13][C:6]2[C:7]([CH2:10][CH2:11][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)=[CH:8][O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 118307868-(1-piperazinyl)QuinolineHCID 236144453-(2-Iodoethyl)-6-methoxy-1-benzofuran

Product 1

HCID 112461978-{4-[2-(6-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-(6-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. 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 eluting it initially with 70% ethyl acetate:hexane and then with 5% methanol:ethyl acetate. 8-{4-[2-(6-methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline was isolated as yellow oil. Yield: 120 mg (31%); (M+H): 388; 1HNMR (400 MHz, CDCl3): δ□8.82˜8.81 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 8.05˜8.02 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H); 7.44˜6.35 (m, 8H); 3.9 (s, 3H); 3.60˜2.70 (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 eluting it initially with 70% ethyl acetate

Sources & evidence

ORD record
ord-2be855979a1f4cc19d53db6736b4c4e7
Source dataset
uspto-grants-2007_10
Patent number
US07276603B2

Reaction notes

Loading…