HCID 86616768, compound → HCID 86616769, compound

HRID 1784360Notes

Reaction equation

HRID 1784360 reaction equation
[C:1]([C:3]([C:24]#[N:25])=[C:4]([N:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)#[N:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:5]1([C:4]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[C:3]([C:1]#[N:2])[C:24]#[N:25])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 86616768HCID 86616768, compound

Product 1

HCID 86616769HCID 86616769, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(2,2-dicyano-1-phenylvinyl)piperazine-1-carboxylate (2 g) was dissolved in a 33.3% solution of TFA in methylene chloride (20 ml). After 16 hour at room temperature, solvents were removed under vacuum to offer a residue which was purified using silica gel chromatography to give 2-(phenyl(piperazin-1-yl)methylene)malononitrile (1 g). 1H NMR (500 MHz, CD3OD) □7.62 (m, 5H), 3.70 (b, 4H), 3.47 (b, 4H); 13C NMR (125 MHz, CD3OD) □172.9, 132.7, 132.5, 129.6, 116.6, 116.0, 55.2, 43.4. MS m/z: (M+H)+ calcd for C14H15N4 239.13, found 239.13. Retention time 0.56 min (column A).

Workup

  1. customsolvents were removed under vacuum
  2. customwas purified

Sources & evidence

ORD record
ord-3281829e234c47e6b97845298d15f7f6
Source dataset
uspto-grants-2009_03
Patent number
US07504399B2

Reaction notes

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