Diisopropylethylamine → 8-{4-[2-(7-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline

HRID 1178813ノート

反応式

HRID 1178813 の反応式
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13]I)[C:7]=2[CH:6]=[CH:5][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[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH2:13][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:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 118307868-(1-piperazinyl)QuinolineHCID 236144473-(2-Iodoethyl)-7-methoxy-1-benzofuran

生成物 1

HCID 112345928-{4-[2-(7-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of 2-(7-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 low melting solid was purified by silica-gel column chromatography by initially eluting it with 70% ethyl acetae:hexane and then with 5% methanol:ethyl acetate. 8-{4-[2-(7-methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-quinoline was isolated as a dark brown low melting solid. Yield: (HCl salt) 90 mg (21%); (M+H): 388; 1H NMR: δ□11.9 (bs, 1H), 9.2 (d, 1H), 9.0 (bs 1H), 8.2 (m, 2H), 7.9 (s1H), 7.84 (m, 2H), 7.45 (d, 1H), 7.21 (t, 1H), 6.98 (d, 1H), 4.01 9s, 3H), 3.77 (m, 4H), 3.67 9m, 2H), 3.59 (m, 4H), 3.3 (m, 2H).

後処理

  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 low melting solid was purified by silica-gel column chromatography
  8. washby initially eluting it with 70% ethyl acetae

出典と根拠

ORDレコード
ord-563ad77881e945b0bea6ec33dbbbe32a
出典データセット
uspto-grants-2007_10
特許番号
US07276603B2

反応ノート

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