Formaldehyde → 2-(4-Methylpiperazin-1-yl)benzonitrile

HRID 650987Notes

Reaction equation

HRID 650987 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)#[N:2].[CH2:15]=O>C(O)=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)#[N:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 2735875N-(2-Cyanophenyl)piperazine

Product 1

HCID 130481902-(4-Methylpiperazin-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

7.48 g of 1-(2-cyanophenyl)-piperazine are refluxed for one hour with 30 ml of formaldehyde and 30 ml of formic acid. The solvents are evaporated in vacuo and the residue is taken up in ether and mixed with water. The mixture is made alkaline with 20% sodium hydroxide solution, saturated with potassium carbonate and extracted with ether. The organic phase is dried over sodium sulphate and concentrated by evaporation in vacuo. To purify the residue it is chromatographed on silica gel with ethyl acetate/isopropanol (70:30, mixed with 1% of a 25% ammonia solution). Yield: 6.7 g (83% of theory).

Workup

  1. customThe solvents are evaporated in vacuo
  2. additionmixed with water
  3. extractionsaturated with potassium carbonate and extracted with ether
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. customTo purify the residue it
  7. customis chromatographed on silica gel with ethyl acetate/isopropanol (70:30
  8. additionmixed with 1% of a 25% ammonia solution)

Sources & evidence

ORD record
ord-b23042be64004227b9c6001113d333ca
Source dataset
uspto-grants-2001_08
Patent number
US06277872B1

Reaction notes

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