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

HRID 736117

반응식

HRID 736117 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-76b19fc017a945dbb8eb74112f1ddbd5
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595314B2

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