HCID 68868816, compound → HCID 68870203, compound

HRID 1784362Notes

Reaction equation

HRID 1784362 reaction equation
[C:1]([CH:3]=[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[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[CH:3][C:1]#[N:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 68868816HCID 68868816, compound

Product 1

HCID 68870203HCID 68870203, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(2-cyano-1-phenylvinyl)piperazine-1-carboxylate (600 mg) was dissolved in a 10% solution of TFA in methylene chloride (11 ml). After 1 hour at room temperature, the reaction mixture was partitioned between saturated NaHCO3 (20 ml) and EtOAc (20 ml), and the aqueous phase was extracted with EtOAc (3×20 ml). Then the combined organic layer was dried over MgSO4 and concentrated to offer a residue which was purified using silica gel chromatography to give 3-phenyl-3-(piperazin-1-yl)acrylonitrile. MS m/z: (M+H)+ calcd for C13H16N3 214.13, found 214.15. Retention time 0.91 min (column E).

Workup

  1. customthe reaction mixture was partitioned between saturated NaHCO3 (20 ml) and EtOAc (20 ml)
  2. extractionthe aqueous phase was extracted with EtOAc (3×20 ml)
  3. dry with materialThen the combined organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customwas purified

Sources & evidence

ORD record
ord-d21f6c4402e3420d8dff6e16a32fcaae
Source dataset
uspto-grants-2009_03
Patent number
US07504399B2

Reaction notes

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