Potassium Carbonate → Tert-butyl 4-(3-chloro-2-cyanophenyl)piperazine-1-carboxylate

HRID 1592723Notes

Reaction equation

HRID 1592723 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)C>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:15]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:16]=2[C:17]#[N:18])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 695872-Chloro-6-fluorobenzonitrileHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 17952290Tert-butyl 4-(3-chloro-2-cyanophenyl)piperazine-1-carboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-Boc-piperazine (2.02 g, 11.0 mmol) in DMSO (20 mL) was added 2-fluoro-6-chlorobenzonitrile (1.55 g, 10 mmol) and potassium carbonate (1.52 g, 11 mmol). The mixture was stirred at 80° C. for about 48 hours. The mixture was cooled to r.t. and diluted with diethyl ether (200 mL). The solution was washed with 1N HCl (2×20 mL), H2O (3×20 mL) and brine (20 mL) and then dried over sodium sulfate and concentrated to a yellow oil. Purification by flash chromatography (4:1 hexanes/ethyl acetate) gave the title compound (2.5 g, 86%) as a colorless oil.

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. washThe solution was washed with 1N HCl (2×20 mL), H2O (3×20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to a yellow oil
  5. customPurification by flash chromatography (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5ccec1ad9e8a40f68309c1e1b7535920
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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