1,3-Dibromobenzene → tert-Butyl 4-(3-bromophenyl)piperazine-1-carboxylate

HRID 45698

反応式

HRID 45698 の反応式
N1CCC[C@H]1C(O)=O.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25](Br)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[Br:22][C:23]1[CH:24]=[C:25]([N:12]2[CH2:13][CH2:14][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:11]2)[CH:26]=[CH:27][CH:28]=1

参加物

7

反応物 4

HCID 79271,3-DibromobenzeneHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 145742L-Proline

生成物 1

HCID 10882380tert-Butyl 4-(3-bromophenyl)piperazine-1-carboxylate

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed copper(I) iodide (1.0 g, 5.26 mmol, 0.20 equiv), L-proline (930 mg, 8.09 mmol, 0.30 equiv) in DMSO (50 mL). The resulting solution was stirred for 15 min at room temperature. Then, tert-butyl piperazine-1-carboxylate (5 g, 26.88 mmol, 1.00 equiv), 1,3-dibromobenzene (9.5 g, 40.25 mmol, 1.50 equiv), potassium carbonate (7.4 g, 53.62 mmol, 1.99 equiv) was added. The resulting solution was stirred overnight at 90° C. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 2×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:6). This resulted in 2.9 g of tert-butyl 4-(3-bromophenyl)piperazine-1-carboxylate as a white solid.

後処理

  1. customInto a 250-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred overnight at 90° C
  4. customThe reaction was then quenched by the addition of 100 mL of water
  5. extractionThe resulting solution was extracted with 2×100 mL of ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 2.9 g of tert-butyl 4-(3-bromophenyl)piperazine-1-carboxylate as a white solid

出典と根拠

ORDレコード
ord-c64ae6e5d8b24249b350bd014dc70f64
出典データセット
uspto-grants-2013_09
特許番号
US08541448B2

関連ノート

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