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Water → Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate

HRID 1066177
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1066177
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[CH:35]=[CH:34][C:14]([C:15]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:18]=3)=[O:16])=[CH:13][C:12]=2O)=[CH:5][CH:4]=1)[CH3:2].C(=O)([O-])[O-:38].[K+].[K+].[Cl:43][CH:44](Br)[CH2:45][CH3:46].O>CN(C)C=O.C(OCC)(=O)C>[Cl:43][CH2:44][CH2:45][CH2:46][O:38][C:13]1[CH:12]=[C:11]([NH:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH:35]=[CH:34][C:14]=1[C:15]([C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:18]=1)=[O:16]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-HCID 21197979Ethyl 4-{3-[4-(4-ethylphenyl)methylamino-3-hydroxybenzoyl)indol-1-yl}butanoate

Produkt 1

HCID 21197980Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 4-{3-[4-(4-ethylphenyl)methylamino-3-hydroxybenzoyl]indol-1-yl}butanoate (39.3 g) was dissolved in N,N-dimethylformamide (200 ml), and potassium carbonate (22.4 g) and chlorobromopropane (24 ml) were added to the solution. The mixture was stirred at room temperature for four hours. The reaction mixture was poured into water, and ethyl acetate was further added for extraction. The formed organic layer was sequentially washed with 1N hydrochloric acid, saturated sodium bicarbonate, and brine, and dried. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby obtain 44.8 g of ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate as a yellow oil. MS(m/z): 562(MH+); IR(CHCl3)cm−1:3450, 1730, 1595; NMR(CDCl3)δ:1.21(t, 3H), 1.25(t, 3H), 2.13˜2.36(m, 6H), 2.66(q, 2H), 3.72(t, 2H), 4.10(q, 2H), 4.21˜4.31(m, 4H), 4.43(d, 2H), 5.03(t, 1H), 6.59(d, 1H), 7.08˜7.50(m, 9H), 7.60(s, 1H), 8.31˜8.37(m, 1H).

Aufarbeitung

  1. additionwas further added for extraction
  2. washThe formed organic layer was sequentially washed with 1N hydrochloric acid, saturated sodium bicarbonate, and brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-f04b72c3d9404e88863adc4b743dbfdd
Quelldatensatz
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06242449B1

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