Chloroacetonitrile → 1-(1,4-Benzodioxan-5-yl)-4-cyanomethylpiperazine

HRID 1290780Notes

Reaction equation

HRID 1290780 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.[CH2:17]([N:19](CC)CC)[CH3:18].ClCC#N>CN1CCCC1=O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:18][C:17]#[N:19])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 65853Eltoprazine

Product 1

HCID 106112891-(1,4-Benzodioxan-5-yl)-4-cyanomethylpiperazine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-(1,4-benzodioxan-5-yl)piperazin (11 g) and triethylamine (7 ml) in N-methyl-2-pyrrolidinone was treated dropwise with chloroacetonitrile (4.5 g). After stirring for 2 h at 100° C. the mixture was poured onto ice and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The product, 1-(1,4-benzodioxan-5-yl)-4-cyanomethylpiperazine, was obtained as an oil (17.4 g) which was sufficiently pure for use in the next step.

Workup

  1. additionwas poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eeb312d2a22e48b48f084c41e02aa3f8
Source dataset
uspto-grants-1998_05
Patent number
US05753661

Reaction notes

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