Chloroacetonitrile → 4-(2-Oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetonitrile

HRID 2417595Notes

Reaction equation

HRID 2417595 reaction equation
C(O)(=O)C.[N:5]1([C:11]2[C:12](=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Cl[CH2:20][C:21]#[N:22].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:18]=[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=[C:11]1[N:5]1[CH2:6][CH2:7][N:8]([CH2:20][C:21]#[N:22])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 195997252-(1-Piperazinyl)-2,4,6-cycloheptatrien-1-one acetate

Product 1

HCID 155921014-(2-Oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-acetonitrileYield 20.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one acetate (10.0 g, described in Example 2), chloroacetonitrile (13.2 g) and potassium carbonate (14.5 g) in acetonitrile (110 ml) was stirred at room temperature for 16 hr, and filtered. The filtrate was evaporated. The residue was chromatographed on silica gel (300 g) using ethyl acetate-acetone (4:1) give 1.9 g of the title compound, which was then crystallized from acetone-diethyl ether: mp 133°-135° C.; ir(CHCl3) 2230 and 1565 cm-1 ; uv max(MeOH) 350 (ε=9810), 254 (ε=14575) and 222 nm(ε=11960); nmr(CDCl3) δ2.75 (t, 4H), 3.4 (t, 4H), 3.55 (s, 2H) and 7.0 (m, 5H); and Anal. Calcd for C13H15N3O: C, 68.4% H, 6.56% N, 18.38% and Found: C, 68.15% H, 6.68% N, 18.25%.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel (300 g)

Sources & evidence

ORD record
ord-af950d9144834754852f024da62a95b8
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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