Potassium Carbonate → Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate

HRID 1181623

反応式

HRID 1181623 の反応式
F[C:2]1(C)[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH2:3]1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[N+:8]([C:4]1[CH:3]=[C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 694220641-Fluoro-3-nitrotoluene

生成物 1

HCID 22330126Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate収率 413.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

5.0 g (3.54 mmol) of 1-fluoro-3-nitrotoluene, 9.89 g (5.31 mmol) of tert-butyl 1-piperazinecarboxylate and 27.0 g (19.5 mmol) of potassium carbonate are solubilized under an argon atmosphere in DMSO (60 ml), then the reaction medium is taken to 100° C. for 72 hours. The reaction medium is then cooled down using an ice bath then poured into ice-cold water. The product is extracted using 3 times 50 ml of dichloromethane. The organic solution is dried over magnesium sulphate, followed by filtration and concentration under vacuum. Purification on a silica column is then carried out (eluent=heptane 70%/ethyl acetate 30%) in order to produce a yellow solid. The yellow solid is further purified by recrystallization from diisopropyl ether in order to produce 4.5 g of the expected product (yield 42.0%). Melting point: 82.0-92.0° C.

後処理

  1. temperatureThe reaction medium is then cooled down
  2. additionthen poured into ice-cold water
  3. extractionThe product is extracted
  4. dry with materialThe organic solution is dried over magnesium sulphate
  5. filtrationfollowed by filtration and concentration under vacuum
  6. customPurification on a silica column
  7. customto produce a yellow solid
  8. customThe yellow solid is further purified by recrystallization from diisopropyl ether in order

出典と根拠

ORDレコード
ord-21bedd9c0aed4d8da2a160a08e54103a
出典データセット
uspto-grants-2007_10
特許番号
US07285664B2

関連ノート

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