Methyl 4-bromoacetylphenoxyacetate → Methyl 4-[2-[4-(5,6,7,8-tetrahydro-4-quinolinyl)piperazin-1-yl]-acetyl]phenoxyacetate

HRID 1290481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1290481
Br[CH2:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:17]1([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.N1(C2C3CCCCC=3N=CC=2)CCNCC1>C(#N)C>[N:26]1[C:27]2[CH2:28][CH2:29][CH2:30][CH2:31][C:32]=2[C:23]([N:17]2[CH2:18][CH2:19][N:20]([CH2:2][C:3]([C:5]3[CH:16]=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:21][CH2:22]2)=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 243438Methyl 4-bromoacetylphenoxyacetateHCID 15343864-Piperazin-1-yl-quinolineHCID 189184264-(Piperazin-1-yl)-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 18924099Methyl 4-[2-[4-(5,6,7,8-tetrahydro-4-quinolinyl)piperazin-1-yl]-acetyl]phenoxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Example 1, methyl 4-bromoacetylphenoxyacetate (1.23 g), a 1:1 mixture containing 4-(1-piperazinyl)quinoline and 4-(1-piperazinyl)-5,6,7,8-tetrahydroquinoline (1.84 g) and acetonitrile (56 ml) yielded, after stirring at room temperature overnight, filtration and evaporation of the filtrate, an orange/brown oily residue which was purified by flash chromatography, first on neutral alumina by elution with 5% v/v methanol/dichloromethane, then on silica by elution with methanol/dichloromethane (0.5% v/v to 5% v/v), and finally by crystallisation of the lower Rf material from methanol/water, to yield the title compound (298 mg) as a cream solid: NMR (CDCl3) δ 1.76(2H,m), 1.89(2H,m), 2.64(2H,m), 2.76(4H,m), 2.95(2H,m), 3.07(4H,m), 3.80(2H,s), 3.81(3H,s), 4.71(2H,s), 6.68(1H,d), 6.95(2H,d), 8.03(2H,d), 8.28(1H,d); m/Z 424 (M+H)+ ; calculated for C24H29N3O4.1.0 H2O: C, 65.3%; H, 7.08%; N, 9.52%; found: C, 65.6%; H, 6.7%; N, 9.3%.

Aufarbeitung

  1. customyielded
  2. filtrationfiltration and evaporation of the filtrate
  3. customan orange/brown oily residue which was purified by flash chromatography, first on neutral alumina by elution with 5% v/v methanol/dichloromethane
  4. washon silica by elution with methanol/dichloromethane (0.5% v/v to 5% v/v), and
  5. customfinally by crystallisation of the lower Rf material from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-263e0264238e4aadb7d9def5ba22d2d2
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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