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Bromide ion → tert-Butyl piperazine-1-carboxylate

HRID 392383
Notes
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Reaction equation

HRID 392383 reaction equation
BrC1C=CC=CC=1OC1C=CC=CC=1Br.C([C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])(C)(C)C.[CH3:28][C:29]([CH3:32])([O-:31])[CH3:30].[Na+].[Br-]>C1(C)C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([O:31][C:29]([CH3:32])([CH3:30])[CH3:28])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 259Bromide ionHCID 27614081-(2,2-dimethylpropanoyl)piperazineHCID 34650962,2'-Dibromodiphenyl etherHCID 23676156Sodium t-butoxide

Product 1

HCID 143452tert-Butyl piperazine-1-carboxylateYield 69.6%

Reagents, catalysts & solvents 2

HCID 634876
Binap, (A+-)-
Catalyst
HCID 1140TolueneSolvent

Procedure

Part B: To a solution of the bromophenyl ether of Part A (10.0 g, 41.1 mmol) in toluene (80 mL) was added 1-tert-butylcarbonylpiperazine (Lancaster, 9.2 g, 49.4 mmol) and sodium tert-butoxide (Fluka, 5.5 g, 57.5 mmol). The reaction stirred at ambient temperature for twenty minutes. BINAP (Aldrich, 0.8 g, 1.2 mmol) and tris(dibenzylideacetone)dipalladium (0) (Aldrich, 0.4 g, 0.4 mmol) were then added and the reaction was stirred at 80° C. until the bromide was exhausted. Work up comprised cooling the mixture to ambient temperature, filtering through a Celite® pad, and concentrating the filtrate. The resulting residue was purified on silica gel (ethyl acetate/hexanes) to afford the BOC-piperazine as a black oil (6.4 g, 44% yield). 1H NMR showed the desired compound.

Workup

  1. temperatureWork up comprised cooling the mixture to ambient temperature
  2. filtrationfiltering through a Celite® pad
  3. concentrationconcentrating the filtrate
  4. customThe resulting residue was purified on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4bb5208ee51a4007a19a69b29bd184e9
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06800646B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes