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Cesium carbonate → Tert-butyl 4-(4-(dibenzylamino)-3-(trifluoromethoxy)phenyl)piperazine-1-carboxylate

HRID 1503863
Notes
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Reaction equation

HRID 1503863 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[O:16][C:17]([F:20])([F:19])[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:28]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][C:12]([N:31]2[CH2:30][CH2:29][N:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32]2)=[CH:11][C:10]=1[O:16][C:17]([F:20])([F:19])[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 70558473N,N-dibenzyl-4-bromo-2-(trifluoromethoxy)aniline

Product 1

HCID 86725404Tert-butyl 4-(4-(dibenzylamino)-3-(trifluoromethoxy)phenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product of EXAMPLE 45A (7.92 g, 18.21 mmol), tert-butyl piperazine-1-carboxylate (3.73 g, 20 mmol), palladium diacetate (205 mg, 0.91 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (850 mg, 1.36 mmol) and cesium carbonate (11.88 g, 36 mmol) in toluene (200 mL) was heated under nitrogen at 100° C. for 20 hours. After cooling to ambient temperature, the mixture was concentrated and the residue was diluted with dichloromethane (300 mL), washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 10/1 petroleum ether/ethyl acetate to give the title compound. MS: 542 (M+H+).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated
  3. additionthe residue was diluted with dichloromethane (300 mL)
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  9. washeluting with 10/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-a254ede152ae46bc96bfc7a45ee399d5
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09212192B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes