1-Tert-butylpiperazine → 1-Phenylpiperazine

HRID 2297590ノート

反応式

HRID 2297590 の反応式
C(O[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1Br)CCC.C([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:6]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

参加物

6

反応物 3

HCID 35305721-Tert-butylpiperazineHCID 190081261-Bromo-2-butoxybenzeneHCID 23676156Sodium t-butoxide

生成物 1

HCID 70961-Phenylpiperazine収率 157.1%

試薬・触媒・溶媒 2

HCID 634876Binap, (A+-)-触媒HCID 1140Toluene溶媒

実験手順

Part A: To a solution of n-butyloxybromobenzene (5.00 g, 21.82 mmol) in toluene (50 mL) was added tert-butyl piperazine (4.88 g, 26.18 mmol) and sodium tert-butoxide (2.94 g, 30.55 mmol). After stirring at ambient temperature for several minutes, BINAP (0.408 g, 0.655 mmol) and tris(dibenzyldeneacetone)-dipallidium (0) (0.200 g, 0.218 mmol) were added. The resulting mixture was heated to eighty degrees Celsius for 21 hours. After cooling to ambient temperature, the reaction mixture was filtered through a pad of Celite®, washing with diethyl ether and dichloromethane. Chromatography (on silica, ethyl acetate/hexanes) provided the phenyl-piperazine as a tan solid (5.56 g, 76%).

後処理

  1. temperatureThe resulting mixture was heated to eighty degrees Celsius for 21 hours
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe reaction mixture was filtered through a pad of Celite®
  4. washwashing with diethyl ether and dichloromethane

出典と根拠

ORDレコード
ord-57d6173298034604bd9735ba369e20f5
出典データセット
uspto-grants-2002_12
特許番号
US06492367B1

反応ノート

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