1-Butanol → 1-Piperazinebutanenitrile, 4-(2-pyrimidinyl)-

HRID 745209Notes

Reaction equation

HRID 745209 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[N:7]1[CH:12]=[CH:11][CH:10]=[N:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[Na+].[Na+].C(O)CCC>O>[C:5]([CH2:4][CH2:3][CH2:2][N:16]1[CH2:17][CH2:18][N:13]([C:8]2[N:9]=[CH:10][CH:11]=[CH:12][N:7]=2)[CH2:14][CH2:15]1)#[N:6]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 10340Sodium CarbonateHCID 123364-ChlorobutyronitrileHCID 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 3986541-Piperazinebutanenitrile, 4-(2-pyrimidinyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chlorobutyronitrile (3.3 g; 0.032 mol), 1-(2-pyrimidinyl)piperazine (3.3 g; 0.032 mol), sodium carbonate (6.4 g; 0.0608 mol) and n-butanol (50 ml) was heated under reflux for 19 hours. After completion of the reaction, the resultant mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography to give 1-(3-cyanopropyl)-4-(2-pyrimidinyl)-piperazine. M.P., 56°-57° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6648ebb3fd8e4c8099da983c5c0a5785
Source dataset
uspto-grants-1986_07
Patent number
US04598078

Reaction notes

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