4-Iodoaniline → Tert-butyl 4-(4-aminophenyl)-3-oxopiperazine-1-carboxylate

HRID 1783987

反応式

HRID 1783987 の反応式
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][C:18](=[O:22])[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Cu]I>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[C:18](=[O:22])[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

参加物

6

反応物 3

HCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

生成物 1

HCID 57437534Tert-butyl 4-(4-aminophenyl)-3-oxopiperazine-1-carboxylate収率 87%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
119 °C

実験手順

A suspension of p-iodo-aniline (918 mg, 4.8 mmol), 3-oxo-piperazine-1-carboxylic acid tert-butyl ester (960 mg, 4.2 mmol) (1R,2R)-cyclohexane-1,2-diamine (0.05 mL, 0.42 mmol), copper (I) iodide (14.9 mg, 0.0042 mmol) and K2CO3 (1.19 g, 2.04 mmol) in dioxane (4 mL), is purged with nitrogen for 5 min in a reaction tube. The tube is sealed and the reaction mixture is heated at 119° C. for 15 hours. After cooling to room temperature, the reaction mixture is filtered through a silica cartridge washing with ethyl acetate (40 mL). The filtrate is concentrated in vacuo to afford the title compound as a brown liquid (1.06 g, 87%). LCMS: Rt 0.88 min (91%).

後処理

  1. customis purged with nitrogen for 5 min in a reaction tube
  2. customThe tube is sealed
  3. temperatureAfter cooling to room temperature
  4. filtrationthe reaction mixture is filtered through a silica cartridge
  5. washwashing with ethyl acetate (40 mL)
  6. concentrationThe filtrate is concentrated in vacuo

出典と根拠

ORDレコード
ord-d3d356812b1f43bf9733b56ece81d4c4
出典データセット
uspto-grants-2009_03
特許番号
US07501411B2

関連ノート

読み込み中…