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Dimethyl Sulfoxide → Tert-butyl 4-(6-bromoquinolin-4-yl)piperazine-1-carboxylate

HRID 1792436
ノート
印刷プレビュー

反応式

HRID 1792436 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C.CS(C)=O>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:16]1[CH2:15][CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 51395376-Bromo-4-chloroquinoline

生成物 1

HCID 22031412Tert-butyl 4-(6-bromoquinolin-4-yl)piperazine-1-carboxylate収率 71.7%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 243 mg 6-bromo-4-chloroquinoline, 373 mg t-butyl 1-piperazine carboxylate, 0.28 mL triethylamine and 10 mL dimethyl sulfoxide was stirred at 80° C. overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed twice with water and then with brine and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 282 mg of the title compound as a pale yellow oil.

後処理

  1. customthe organic layer was separated
  2. washwashed twice with water
  3. dry with materialwith brine and dried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-27070b7657314989abb352220f1b84f4
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07074801B1

反応ノート

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