Potassium Carbonate → HCID 54531367, compound

HRID 582551Notes

Reaction equation

HRID 582551 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:16][CH2:17][C:18]#[N:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][C:18]#[N:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 54247840HCID 54247840, compound

Product 1

HCID 54531367HCID 54531367, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(tert-butyloxycarbonyl)piperazine (1.73 g, 9.3 mmol), 4-bromo-4-phenylbutyronitrile (2.5 g, 11 mmol) and K2CO3 (1.4 g, 10.2 mmol) in DMF (40 mL) was heated at 60° C. for 4 h. After this time the mixture was cooled to room temperature, filtered and the filtrate evaporated. The residue was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (2:1). The piperazine (2.69 g, 88%) was isolated as a pale yellow oil, which solidified on standing in the fridge. 1H NMR (250 MHz, CDCl3) δ1.41 (9H, s), 1.94-2.46 (8H, m), 3.32-3.60 (5H, m), 7.15-7.42 (5H, m). MS (ES+) (330, M+1).

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between EtOAc (100 mL) and water (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with petrol:EtOAc (2:1)

Sources & evidence

ORD record
ord-df2973ac3e554307beb29dee16328407
Source dataset
uspto-grants-1999_07
Patent number
US05925638

Reaction notes

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