Triethylamine → 4-Amino-6,7-dimethoxy-2-[4-(isobutoxycarbonyl)-piperazin-1-yl]quinoline hydrochloride sesquihydrate

HRID 542210

Reaktionsgleichung

Reaktionsgleichung von HRID 542210
[CH2:1]([O:5][C:6]([Cl:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:11]=1.C(N(CC)CC)C.C(=O)([O-])[O-:38].[Na+].[Na+]>C(Cl)(Cl)Cl>[OH2:5].[ClH:8].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:25][CH2:26][N:27]([C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:7])[CH2:28][CH2:29]2)[CH:11]=1.[OH2:38].[OH2:5].[NH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[C:12]([N:24]2[CH2:25][CH2:26][N:27]([C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:7])[CH2:28][CH2:29]2)[CH:11]=1.[ClH:8]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 62365Isobutyl chloroformateHCID 140689984-Amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline

Produkt 1

HCID 1317150914-Amino-6,7-dimethoxy-2-[4-(isobutoxycarbonyl)-piperazin-1-yl]quinoline hydrochloride sesquihydrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A solution of isobutylchloroformate (0.11 g) in chloroform (5 ml) was added dropwise to a stirred solution of 4-amino-6,7-dimethoxy-2-[piperazin-1-yl]quinoline (0.21 g) in chloroform (15 ml) with triethylamine (0.22 g) at 10°. The solution was then stirred at room temperature for 1 hour and sodium carbonate solution (10%, 10 ml) added. The organic phase was separated, the aqueous solution extracted with chloroform (2×15 ml) and the total combined extracts dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography on silica gel (Merck 9385, 25 g) eluting with methylene chloride-methanol (100:0→93:7), followed by treatment of the product with ethereal hydrogenchloride and recrystallisation from isopropanol to give 4-amino-6,7-dimethoxy-2-[4-(isobutoxycarbonyl)-piperazin-1-yl]quinoline hydrochloride sesquihydrate, m.p. 254°-256° (0.065 g).

Aufarbeitung

  1. customThe organic phase was separated
  2. extractionthe aqueous solution extracted with chloroform (2×15 ml)
  3. dry with materialthe total combined extracts dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel (Merck 9385, 25 g)
  6. washeluting with methylene chloride-methanol (100:0→93:7)
  7. customfollowed by treatment of the product with ethereal hydrogenchloride and recrystallisation from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-c43c6bccb2c34bc69377397fd77818c3
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04656174

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