2-Methoxy-2,4,6-cycloheptatrien-1-one → HCID 15592102, compound

HRID 2417594Notes

Reaction equation

HRID 2417594 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O:15][C:16]1[C:17](=O)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1>CO>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:22]3[C:16](=[O:15])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 165462-Methoxy-2,4,6-cycloheptatrien-1-oneHCID 759941-Benzylpiperazine

Product 1

HCID 15592102HCID 15592102, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(phenylmethyl)-piperazine (3.2 g) and 2-methoxy-2,4,6-cycloheptatrien-1-one (1.6 g) in methanol (6 ml) was refluxed for 10 hr and evaporated. The residue was dissolved in a mixture of chloroform and water. The organic phase was separated, dried and evaporated. The residue was chromatographed on silica gel (200 g) using methanol-chloroform (5:95). The eluates were evaporated to give the title compound (2.7 g): mp 78°-80° C.; ir(CHCl3) 2400, 1705, 1620, 1350 and 1570 cm-1 ; uv max(MeOH) 343 (ε=9440) and 250 nm (ε=14975); nmr(CDCl3) δ2.9 (s, 3H), 3.5 (m, 8H), 6.27 (s, 2H), 7.0 (m, 5H) and 14.5 (broad, 2H); and Anal. Calcd for C18H20N2O2 : C, 77.11% H, 7.19% N, 9.99% and Found: C, 77.08% H, 7.17% N, 9.74%.

Workup

  1. temperaturewas refluxed for 10 hr
  2. customevaporated
  3. dissolutionThe residue was dissolved in a mixture of chloroform and water
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (200 g)
  8. customThe eluates were evaporated

Sources & evidence

ORD record
ord-37108d92c32a472499040ee6ad13f1e3
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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