Tri-o-tolylphosphine → 1-[2-Chloro-4-(trifluoromethyl)phenyl]piperazine

HRID 32650

Reaction equation

HRID 32650 reaction equation
[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([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)(OC(C)(C)C)=O.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O1CCOCC1.CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

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

Product 1

HCID 468374961-[2-Chloro-4-(trifluoromethyl)phenyl]piperazineYield 10%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-81443adcf32b432695227f565089dcc7
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Linked notes

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