Triethylamine → tert-Butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate

HRID 2209167Notes

Reaction equation

HRID 2209167 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:13][CH2:12][N:11]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[C:6]([C:7]#[N:8])[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 56763808tert-Butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a pressure tube, 5-bromo-2-fluorobenzonitrile (2500 mg, 12.5 mmol), tert-butyl piperazine-1-carboxylate (2444.45 mg, 13.12 mmol), triethylamine (5.23 ml, 37.5 mmol) in dimethylsulfoxide (10 ml) were combined and refluxed at 100 C for ovn. The mixture was cooled, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried using sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel 5-60% ethyl acetate/hexane to provide a light brown oil, tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate (3660 mg, 80%).

Workup

  1. temperaturerefluxed at 100 C for ovn
  2. temperatureThe mixture was cooled
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on silica gel 5-60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f7aeb9dea80e4af889c73bab9a226e2c
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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