Potassium Carbonate → 1-Boc-4-(4-Cyanobenzyl)piperazine

HRID 252869Notes

Reaction equation

HRID 252869 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.BrC[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20].[C:24]([O-])([O-])=O.[K+].[K+]>CCO>[C:19]([C:18]1[CH:17]=[CH:16][C:23]([CH2:24][N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[CH:22][CH:21]=1)#[N:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 183822571-Boc-4-(4-Cyanobenzyl)piperazineYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl piperazine-1-carboxylate (334, 1 g, 5.37 mmol), 3-(bromomethyl)benzonitrile (335, 1.26 g, 6.45 mmol) and K2CO3 (1.48 g, 10.74 mmol) in EtOH (20 mU was refluxed for four hours. The reaction mixture was then concentrated, diluted with EtOAc (20 ml.) and washed with water (20 mL). The organic phase was separated, dried with Na2SO4, filtered and concentrated. Crude product was purified by flash chromatography using the gradient 10%-25% EtOAc in hexanes as an eluent to afford the title compound 336 (1.374 g 85%). MS: calc: 301.3; found: 302.1 (M+H)

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additiondiluted with EtOAc (20 ml.)
  3. washwashed with water (20 mL)
  4. customThe organic phase was separated
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrude product was purified by flash chromatography

Sources & evidence

ORD record
ord-7211e0f4730247f693bbb1d9c79feae1
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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