Hydrochloric Acid → Ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy)benzoyl}indol-1-yl}butanoate hydrochloride

HRID 1066178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066178
[Cl:1]CCCO[C:6]1[CH:30]=[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH2:39][CH3:40])=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:7]=1[C:8]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:11]=1)=[O:9].Cl.[CH3:42][O:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1.[I-].[K+].Cl>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[ClH:1].[CH2:39]([C:36]1[CH:37]=[CH:38][C:33]([CH2:32][NH:31][C:29]2[CH:30]=[CH:6][C:7]([C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:11]=3)=[O:9])=[CH:27][C:28]=2[O:9][CH2:8][CH2:7][CH2:6][N:53]2[CH2:54][CH2:55][N:50]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[O:43][CH3:42])[CH2:51][CH2:52]2)=[CH:34][CH:35]=1)[CH3:40]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 21197980Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate

Produkt 1

HCID 21197984Ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy)benzoyl}indol-1-yl}butanoate hydrochlorideAusbeute 142,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 4-{3-[3-chloropropoxy-4-(4-ethylphenyl)methylaminobenzoyl]indol-1-yl}butanoate (44.5 g) was dissolved in N,N-dimethylformamide (230 ml), and 1-(2-methoxyphenyl)piperazine hydrochloride (36.2 g), potassium iodide (52.5 g), and triethylamine (46 ml) were added to the solution. The resultant mixture was stirred at 90° C. for one hour. The reaction mixture was cooled and poured into ethyl acetate (230 ml) and 1N hydrochloric acid (460 ml) was added. Crystals so precipitated were collected by filtration and recrystallized from 90% ethanol, to thereby obtain 42.6 g of ethyl 4-{3-{4-(4-ethylphenyl)methylamino-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy)benzoyl}indol-1-yl}butanoate hydrochloride as colorless crystals.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. additionwas added
  3. customCrystals so precipitated
  4. filtrationwere collected by filtration
  5. customrecrystallized from 90% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-cea1863352ff43f59f2d54dbee054e4f
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242449B1

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