3-(2-Iodoethyl)-5-methoxy-1-benzofuran → 8-{4-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-isopropyl-quinoline

HRID 1178821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178821
[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.[CH:15]([C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2)([CH3:17])[CH3:16]>>[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:31]3[CH2:32][CH2:33][N:28]([C:26]4[CH:27]=[C:18]([CH:15]([CH3:17])[CH3:16])[CH:19]=[C:20]5[C:25]=4[N:24]=[CH:23][CH:22]=[CH:21]5)[CH2:29][CH2:30]3)[C:7]=2[CH:14]=1

Komponenten

3

Edukt 2

HCID 236144423-(2-Iodoethyl)-5-methoxy-1-benzofuranHCID 689284366-Isopropyl-8-piperazino quinoline

Produkt 1

HCID 111778848-{4-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-isopropyl-quinoline

Versuchsvorschrift

8-{4-[2-(5-methoxy-1-benzofuran-3-yl)ethyl]-1-piperazinyl}-6-isopropyl-quinoline was prepared by generally following the procedure outlined in example 21, step 6, starting from 2-(5-methoxy-1-benzofuran-3-yl)ethyl iodide (301 mg, 1 mmol) and 6-isopropyl-8-piperazino quinoline (255 mg, 1 mmol). The product was purified by silica-gel column chromatography by eluting it initially with 80% ethyl acetate:hexane and then with 5% methanol:ethyl acetate, yielding a brown oil. Yield: 90 mg (20%); (M+H): 430; 1HNMR (400 MHz, CDCl3): δ 8.83˜8.12 (dd, J1=1.8 Hz, J2=1.8 Hz, 1H), 8.08˜804 (dd,J1=1.8 Hz, J2=1.8 Hz, 1H), 7.75˜6.70 (m, 7H), 3.84 (s, 3H), 3.50˜2.86 (m, 12H), 2.90˜3.01 (m, 1H), 1.34˜1.33 (d, 7 Hz, 6H).

Aufarbeitung

  1. customThe product was purified by silica-gel column chromatography
  2. washby eluting it initially with 80% ethyl acetate
  3. customhexane and then with 5% methanol:ethyl acetate, yielding a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-83ee6945ab08470c98357198f924508e
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276603B2

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