Cesium carbonate → Tert-butyl 4-(4-chloro-2-methylphenyl)piperazine-1-carboxylate

HRID 242636

反応式

HRID 242636 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:19]([O:18][C:16]([N:10]1[CH2:15][CH2:14][N:13]([C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[CH3:9])[CH2:12][CH2:11]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 844762-Bromo-5-chlorotolueneHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 66757902Tert-butyl 4-(4-chloro-2-methylphenyl)piperazine-1-carboxylate収率 20%

試薬・触媒・溶媒 2

HCID 9832798Tris(dibenzylideneacetone) dipalladium触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

2-Bromo-5-chlorotoluene (0.82 g, 4 mmol) and tert-Butyl 1-piperazine carboxylate (0.89 g, 2.32 mmol) were added to a solution of tri-t-butyl phosphine (0.033 g, 4 mmol %), tris(dibenzylideneacetone) dipalladium(0) (0.075 g, 2.0 mmol %) and cesium carbonate (1.95 g, 6.0 mmol) in toluene and heated to 80° C. overnight. The reaction mixture was filtered through celite and concentrated in vacuo. The crude product was purified on silica gel (gradient elution from 20% ethyl acetate/hexane to 50% ethyl acetate/hexane) to give the title compound in 20% yield. ESI-MS m/z: 311 (M+1), UV retention time: 3.49 min.

後処理

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified on silica gel (gradient elution from 20% ethyl acetate/hexane to 50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-785768d0ce444ce3800805bba17139b8
出典データセット
uspto-grants-2014_02
特許番号
US08653096B2

関連ノート

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