Acrylonitrile → HCID 23371139, compound

HRID 1899749Notes

Reaction equation

HRID 1899749 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:4][CH2:3]1.CN1CCNCC1.C(#N)C=C.[C:23](Cl)(=[O:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][NH:11][C:23](=[O:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 531671-MethylpiperazineHCID 66986Myristoyl chlorideHCID 783281-(3-Aminopropyl)-4-methylpiperazine

Product 1

HCID 23371139HCID 23371139, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.7 g. (0.03 mol) of N-methyl-N'-(3-aminopropyl)-piperazine (prepared from N-methyl piperazine and acrylonitrile and subsequent reduction to the primary amine) in 200 mL chloroform was cooled down in an ice bath. To this was added 7.3 g. (0.03 mol) of myristoyl chloride dropwise for two hours. The reaction mixture was brought to room temperature and then allowed to react for another four hours. The reaction mixture was treated with 10 g. of sodium bicarbonate in 100 mL water and the separated chloroform layer was washed with water (2×200 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Crystallization from acetonitrile afforded 8 g. (72.3%) of the subject product.

Workup

  1. temperaturewas cooled down in an ice bath
  2. additionTo this was added 7.3 g
  3. customwas brought to room temperature
  4. customto react for another four hours
  5. additionThe reaction mixture was treated with 10 g
  6. washof sodium bicarbonate in 100 mL water and the separated chloroform layer was washed with water (2×200 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customCrystallization from acetonitrile
  11. customafforded 8 g

Sources & evidence

ORD record
ord-1e62a88853a84812ac33a715a923ae53
Source dataset
uspto-grants-1996_11
Patent number
US05573726

Reaction notes

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