Tri-o-tolylphosphine → 4-(2-Chloro-4-trifluoromethylphenyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 736117Notes

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: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]

Participants

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

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

Sources & evidence

ORD record: ord-76b19fc017a945dbb8eb74112f1ddbd5
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595314B2

Reaction notes

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