tert-Butyl piperazine-1-carboxylate → HCID 86664147, compound

HRID 1890392Notes

Reaction equation

HRID 1890392 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.C([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])(C)(C)C.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].ClCCl.C(OCC)(=O)C>[F:9][C:8]([F:11])([F:10])[C:17]([O-:16])=[O:18].[F:9][C:8]([F:11])([F:10])[C:5]1[N:6]=[CH:7][C:2]([NH+:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:3][CH:4]=1

Participants

9

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 86664147HCID 86664147, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-trifluoromethyl-pyridine (1.0 mmol), piperazine-1-carboxylic acid tert-butyl ester (1.2 mmol), sodium tert-butoxide (1.65 mmol), tris-(dibenzylideneacetone)-dipalladium (0.022 mmol) and 2-(dicyclohexylphosphino)-biphenyl (0.064 mmol) are dissolved in dry toluene (5 mL) and the resulting mixture is irradiated in a monomode microwave oven for 30 minutes at 100° C. The reaction is then cooled down to room temperature and ethyl acetate is added (15 mL). The precipitate formed is filtered and the filtrate is concentrated under reduced pressure. The crude product thus obtained is taken up in a minimum volume of dichloromethane (2 mL) and is purified by chromatography over a short silica gel pad (diethyl ether as eluent) to afford the desired product.

Workup

  1. customthe resulting mixture is irradiated in a monomode microwave oven for 30 minutes at 100° C
  2. customThe precipitate formed
  3. filtrationis filtered
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe crude product thus obtained
  6. customis purified by chromatography over a short silica gel pad (diethyl ether as eluent)

Sources & evidence

ORD record
ord-2a691e4fa1d8421d8f0dd328ae77911c
Source dataset
uspto-grants-2013_08
Patent number
US08507474B2

Reaction notes

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