Chloroacetone → 2-[4-(2-Oxopropyl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-one

HRID 2417619Notes

Reaction equation

HRID 2417619 reaction equation
[N:1]1([C:7]2[C:8](=[O:14])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:16][C:17](=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:19]=[C:17]([CH3:18])[CH2:16][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:8](=[O:14])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 155920992-(1-Piperazinyl)-2,4,6-cycloheptatrien-1-one

Product 1

HCID 155921442-[4-(2-Oxopropyl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-oneYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one (12.4 g), described in Example 2), 1-chloro-2-propanone (5.55 g), potassium carbonate (11.04 g) and acetonitrile (120 ml) was refluxed for 4 hr and filtered. Chloroform and water were added to the filtrate. The organic phase was separated, washed with water, dried and evaporated. The residue was chromatographed on silica gel using methanol-ethyl acetate and the eluates were evaporated to give an oil (6.21 g) of 2-[4-(2-oxopropyl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-one (VII; R1, R2, R3 and R4 =H and Alk=C--CH2): ir(CHCl3) 3660, 3360, 1720, 1710, 1660 and 1560 cm-1 ; uv max(MeOH) 351 (ε=9310), 255 (ε=13915) and 221 nm(ε=11750); nmr(CDCl3) δ2.12 (s, 3H), 2.62 (t, 4H), 3.21 (s, 2H), 3.35 (s, 4H) and 6.40-7.10 (m, 5H); and Anal. Calcd for C14H18N2O2 : C, 68.26% H, 7.37% N, 11.37% and Found: C, 67.33% H, 7.59% N, 11.44%.

Workup

  1. temperaturewas refluxed for 4 hr
  2. filtrationfiltered
  3. additionChloroform and water were added to the filtrate
  4. customThe organic phase was separated
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed on silica gel
  9. customthe eluates were evaporated

Sources & evidence

ORD record
ord-3f34eb94691f4b558242f31487aa77a5
Source dataset
uspto-grants-1984_09
Patent number
US04469695

Reaction notes

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