Tri-o-tolylphosphine → tert-Butyl 4-[2-chloro-4-(trifluoromethyl)phenyl]piperazine-1-carboxylate

HRID 736117

反応式

HRID 736117 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1I.[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O1CCOCC1.CCOCC>[C:16]([O:15][C:13]([N:20]1[CH2:25][CH2:24][N:23]([C:7]2[CH:6]=[CH:5][C:4]([C:9]([F:12])([F:11])[F:10])=[CH:3][C:2]=2[Cl:1])[CH2:22][CH2:21]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

参加物

7

反応物 4

HCID 80271Tri-o-tolylphosphineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27366123-Chloro-4-iodobenzotrifluorideHCID 23676156Sodium t-butoxide

生成物 1

HCID 53485518tert-Butyl 4-[2-chloro-4-(trifluoromethyl)phenyl]piperazine-1-carboxylate収率 10%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 0.5 g (1.6 mmol) of 3-chloro-4-iodobenzotrifluoride 0.7 g (3.8 mmol), N-Boc-piperazine, 41 mg (0.04 mmol) Tris(dibenzylideneacetone)dipalladium chloroform complex, 0.44 g (4.43 mmol) sodium-t-butoxide and 48 mg (0.16 mmol) tri-o-tolylphosphine in 6 ml dioxane was heated overnight at 100° C. The solution was allowed to cool to room temperature, taken up in ether (30 ml) and washed with brine (25 ml). The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was chromatographed over on silica gel: Eluent: Heptane-AcOEt 0-10% over 15 min to provide the title compound (0.06 g, 10%) as a brown oil, MS (m/e): 365.1 (MH+, 100%).

後処理

  1. temperatureto cool to room temperature
  2. washwashed with brine (25 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude oil was chromatographed over on silica gel

出典と根拠

ORDレコード
ord-76b19fc017a945dbb8eb74112f1ddbd5
出典データセット
uspto-grants-2009_09
特許番号
US07595314B2

関連ノート

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