Chloroacetonitrile → HCID 24693597, compound

HRID 651373Notes

Reaction equation

HRID 651373 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH2:15]([N:17](CC)CC)[CH3:16].ClCC#N>C(#N)C>[C:15]([CH2:16][N:12]1[CH2:13][CH2:14][N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)#[N:17]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 2697221-(4-Methoxyphenyl)piperazine

Product 1

HCID 24693597HCID 24693597, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 19.2 g (100 mmol) of commercially available 4-methoxyphenyl piperazine in acetonitrile (300 ml), 12.1 g (120 mmol) of triethylamine and 7.6 g (100 mmol) of chloroacetonitrile were subsequently added. The reaction mixture was refluxed for 2 hrs, cooled to room temperature and concentrated in vacuo. To the residue dichloromethane (300 ml) and water (150 ml) were added, the water layer was further extracted with dichloromethane (50 ml), the combined organic layers were dried over sodiumsulphate and concentrated in vacuo. In this manner 18.5 g of 1-(cyanomethyl)-4-(4-methoxyphenyl) piperazine (80%) was obtained as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hrs
  2. concentrationconcentrated in vacuo
  3. additionTo the residue dichloromethane (300 ml) and water (150 ml) were added
  4. extractionthe water layer was further extracted with dichloromethane (50 ml)
  5. dry with materialthe combined organic layers were dried over sodiumsulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42405e5105744a41a3c45410ce5ef491
Source dataset
uspto-grants-2001_08
Patent number
US06281216B1

Reaction notes

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