Potassium Carbonate → HCID 58780610, compound

HRID 1376023Notes

Reaction equation

HRID 1376023 reaction equation
Br[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])[C:3]#[N:4].C([O-])([O-])=O.[K+].[K+].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CC#N.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([CH:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:11])[C:3]#[N:4])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 18934784HCID 18934784, compound

Product 1

HCID 58780610HCID 58780610, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bromo-(2-chloro-phenyl)-acetonitrile (1)(1.5 g, 6.45 mmol) in MeCN (25 mL) was added K2CO3 (1.78 g, 12.91 mmol), piperazine-1-carboxylic acid tert-butyl ester (1.32 g, 7.10 mmol) and tetrabutylammonium iodide (0.02 g, 0.06 mmol). The reaction mixture was allowed to reflux for 24 h. The reaction mixture was then diluted with EtOAc (100 mL) and washed with brine (100 mL). The organic phase was concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with a gradient of 5% EtOAc in hexanes to 1:1 hexanes/EtOAc) yielding 1.4 g (65%) of pure product.

Workup

  1. temperatureto reflux for 24 h
  2. washwashed with brine (100 mL)
  3. concentrationThe organic phase was concentrated to dryness
  4. customThe crude material was purified by chromatography (silica gel 60 mesh
  5. washeluting with a gradient of 5% EtOAc in hexanes to 1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-703dec833ad345b5b18177175f01b22a
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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