Piperazine → 2-(Piperazin-1-yl)pyridine-4-carbonitrile

HRID 276779Notes

Reaction equation

HRID 276779 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[C:5]#[N:6].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>>[N:10]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=2)[C:5]#[N:6])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 162279862-(Piperazin-1-yl)pyridine-4-carbonitrileYield 28.4%

Procedure

2-Chloro-isonicotinonitrile (80 g, 0.58 mol) and piperazine (199 g, 2.32 mol, 5 equiv) were combined and heated at 70 DC for 2.5 hours. The resulting suspension was cooled to room temperature and partitioned between a solution of 50% ethyl acetate/dichloromethane and water. The organic phase was separated, and the aqueous phase was extracted with dichloromethane. The combined organic phases were concentrated in vacuo to about half the initial volume and ether was added. The suspension was stirred overnight, then filtered. The solid was dried under vacuum to give the desired product (31 g). The mother liquors were concentrated in vacuo and the residue was triturated with ether and filtered. The solid collected in this second batch was dried under vacuum and combined with the first batch to give the total amount of desired product (46 g, 42%).

Workup

  1. temperatureheated at 70 DC for 2.5 hours
  2. custompartitioned between a solution of 50% ethyl acetate/dichloromethane and water
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. concentrationThe combined organic phases were concentrated in vacuo to about half the initial volume and ether
  6. additionwas added
  7. filtrationfiltered
  8. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-744f8038a3a9425696ce03a32d04e00f
Source dataset
uspto-grants-2002_03
Patent number
US06355635B1

Reaction notes

Loading…