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Diethyl Ether → 2-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-isobutyric acid, dihydrobromide

HRID 1290512
ノート
印刷プレビュー

反応式

HRID 1290512 の反応式
[Br:1][CH2:2][C:3]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13]C)=[O:12])=[CH:7][CH:6]=1)=[O:4].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C.C(OCC)C>C(#N)C>[BrH:1].[BrH:1].[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][N:28]([CH2:2][C:3]([C:5]3[CH:18]=[CH:17][C:8]([O:9][C:10]([CH3:16])([CH3:15])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=3)=[O:4])[CH2:29][CH2:30]2)=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 18918561Methyl 2-(4-bromoacetylphenoxy)isobutyrate

生成物 1

HCID 1317201052-[4-[2-[4-(4-Pyridyl)piperazin-1-yl]acetyl]phenoxy]-isobutyric acid, dihydrobromide

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒
2 回

実験手順

The product from step (i) above (2.00 g) in acetonitrile (10 ml) was added dropwise over 15 minutes to a stirred solution of 1-(4-pyridyl)piperazine (1.04 g) and triethylamine (0.89 ml) in acetonitrile (15 ml) and the mixture stirred overnight. The precipitated solid was removed by filtration and the filtrate evaporated. Purification of the residue by flash chromatography on silica, eluting with 0 to 5% v/v methanol/dichloromethane, gave a yellow gum. Trituration of this gum with diethyl ether gave methyl 2-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenoxy]isobutryate, 170 mg, as a white solid: m.p. 88°-90° C.; NMR (d6 DMSO)δ8.15(2H,d), 7.96(2H,d), 6.82(4H,m), 3.92(2H,s), 3.70(3H,s), 3.33(4H,t), 2.63(4H,t), 1.60(6H,s); m/e 398 (M+H)+ ; calculated for C22H27N3O4.0.25H2O: C, 65.8; H, 6.8; N, 10.5. found: C, 65.8 H, 7.1; N, 10.4%.

後処理

  1. customThe precipitated solid was removed by filtration
  2. customthe filtrate evaporated
  3. customPurification of the residue by flash chromatography on silica
  4. washeluting with 0 to 5% v/v methanol/dichloromethane
  5. customgave a yellow gum

出典と根拠

ORDレコード
ord-3ff2aca72d3145f89c5a3df08b534f28
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05750754

反応ノート

読み込み中…

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