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

HRID 864786

反応式

HRID 864786 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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) δ1.76 (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%.

後処理

  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

出典と根拠

ORDレコード
ord-434a6d501beb4a898364ec078ee92640
出典データセット
uspto-grants-1996_10
特許番号
US05563141

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