1-(2-Hydroxyethyl)piperazine → 2-[4-(2-Hydroxyethyl)piperazin-1-yl]cyclohepta-2,4,6-trien-1-one

HRID 2417599Notes

Reaction equation

HRID 2417599 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.CO[C:12]1[C:13](=[O:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1>CO>[O:19]=[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=[C:12]1[N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 165462-Methoxy-2,4,6-cycloheptatrien-1-one

Product 1

HCID 155921092-[4-(2-Hydroxyethyl)piperazin-1-yl]cyclohepta-2,4,6-trien-1-oneYield 51.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2-hydroxyethyl)piperazine (10.0 g) and 2-methoxy-2,4,6-cycloheptatrien-1-one (10.9 g) in methanol (50 ml) was refluxed for 24 hr and evaporated. The residue was chromatographed on silica gel (100 g) using methanol-ethyl acetate (1:4). The eluates were evaporated and crystallized from ethyl acetate-hexane to give 4-(2-oxo-3,5,7-cycloheptatrien-1-yl)-1-piperazine-ethanol (9.2 g): mp 85°-86° C.; ir(CHCl3) 3440, 1616 and 1555 cm-1 ; nmr(CDCl3) δ2.55 (t, 2H), 2.63 (m, 4H), 3.30 (m, 4H), 3.60 (t, 2H) and 6.40-7.65 (m, 5H); and Anal. Calcd for C13H18N2O2 : C, 66.64% H, 7.74% N, 11.96% and Found: C, 66.12% H, 7.83% N, 11.99%.

Workup

  1. temperaturewas refluxed for 24 hr
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (100 g)
  4. customThe eluates were evaporated
  5. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e22a45669b5143579849b6b20cdaf58b
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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