tert-Butyl piperazine-1-carboxylate → HCID 90239675, compound

HRID 1051907Notes

Reaction equation

HRID 1051907 reaction equation
Cl.[Br:2][C:3]1[C:20]([Br:21])=[CH:19][C:6]2[N:7](C(C)C)[C:8]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:9][C:5]=2[C:4]=1[N+:22]([O-:24])=[O:23].[C:25](N1CCNCC1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CCO>[Br:2][C:3]1[C:20]([Br:21])=[CH:19][C:6]2[NH:7][C:8]([N:10]3[CH2:11][CH2:12][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][CH2:15]3)=[N:9][C:5]=2[C:4]=1[N+:22]([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 75593293HCID 75593293, compound

Product 1

HCID 90239675HCID 90239675, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

2,5,6-tribromo-4-nitro-1H-1,3-benzodiazole (Method 2A) (17.5 mmol, 7 g) was dissolved in EtOH (30 ml) with N-Boc-piperazine (52.5 mmol, 9.78 g). The resulting mixture was stirred at 120° C. until the reaction was complete (8 h) by LC/MS. The mixture was allowed to cool to RT and concentrated in-vacuo. The product was purified on silica gel using DCM/MeOH (99:1) to afford tert-butyl 4-(5,6-dibromo-4-nitro-1H-1,3-benzodiazol-2-yl)piperazine-1-carboxylate (6 g). m/z 405.8; rt 2.4 min.

Workup

  1. custom(8 h)
  2. temperatureto cool to RT
  3. concentrationconcentrated in-vacuo
  4. customThe product was purified on silica gel

Sources & evidence

ORD record
ord-125b6f77aaa74f05816aeda43fc9f83e
Source dataset
uspto-grants-2016_07
Patent number
US09388192B2

Reaction notes

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