o-Bromocumene → 1-(3-Benzyl-phenyl)-2-(S)-isopropyl-4-(2-isopropyl-phenyl)-piperazine

HRID 971374

反応式

HRID 971374 の反応式
[CH2:1]([C:8]1[CH:9]=[C:10]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C@@H:15]2[CH:20]([CH3:22])[CH3:21])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH:30]([CH3:32])[CH3:31].CC([O-])(C)C.[Na+].COCCOC.CCO>C1(C)C=CC=CC=1.CCOCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)C=CC=CC=1>[CH2:1]([C:8]1[CH:9]=[C:10]([N:14]2[CH2:19][CH2:18][N:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH:30]([CH3:32])[CH3:31])[CH2:16][C@@H:15]2[CH:20]([CH3:22])[CH3:21])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 23475o-BromocumeneHCID 20074477Dimethoxyethane ethanolHCID 207600044-(3'-Benzylphenyl)-3-(S)-isopropyl-piperazineHCID 23676156Sodium t-butoxide

生成物 1

HCID 691295551-(3-Benzyl-phenyl)-2-(S)-isopropyl-4-(2-isopropyl-phenyl)-piperazine収率 62.2%

試薬・触媒・溶媒 3

HCID 27349392'-(diphenylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

110.7 mg (0.38 mmol) 4-(3′-Benzylphenyl)-3-(S)-isopropyl-piperazine (88a), 123.5 mg (0.62 mmol, 1.65 eq.) 1-Bromo-2-isopropyl-benzene 11.7 mg (12.7 μmol, 0.034 eq.) Pd2(dba)3, 7.4 mg (19.3 μmol, 0.05 eq.) 2-Diphenylphosphino-2′-dimethylamino-biphenyl and 87.3 mg (0.91 mmol, 2.42 eq.) NaOt-Bu were dissolved in 5 ml dry toluene. The resulting mixture was heated under N2 at 80° C. for 15.5 h. After cooling to room temperature the mixture was diluted with ether and washed with brine. The comb. org. fractions were dried over Na2SO4 and evaporated. Column chromatography (hexanes/EtOAc (9+1)) yielded 96.5 mg (0.23 mmol, 62.20%) 1-(3-Benzyl-phenyl)-2-(S)-isopropyl-4-(2-isopropyl-phenyl)-piperazine (89) as a clear oil.

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. washwashed with brine
  3. dry with materialfractions were dried over Na2SO4
  4. customevaporated

出典と根拠

ORDレコード
ord-22028e2f0fd24a9189311b03f7571aaf
出典データセット
uspto-grants-2007_12
特許番号
US07312246B2

関連ノート

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