Potassium Carbonate → 2-[4-(3-Methoxybenzyl)-1-piperazinyl]-2,4,6-cycloheptatriene-1-one

HRID 609585Notes

Reaction equation

HRID 609585 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.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:8]1[CH2:7][CH2:6][N:5]([C:11]2[C:12](=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699943-Methoxybenzyl chlorideHCID 195997252-(1-Piperazinyl)-2,4,6-cycloheptatrien-1-one acetate

Product 1

HCID 158713422-[4-(3-Methoxybenzyl)-1-piperazinyl]-2,4,6-cycloheptatriene-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(1-piperazinyl)-2,4,6-cycloheptatriene-1-one acetic acid salt (0.171 g, 0.680 mmol, example 2a), 3-methoxybenzyl chloride (0.118 g, 0.750 mmol) and potassium carbonate (0.276 g, 2.00 mmol) in acetonitrile (2.00 mL) was stirred at room temperature for 16 h. The solvent was removed in vacuo. The residue was triturated with dichloromethane and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to preparative thin layer chromatography using ethyl acetate:methanol (9:1) as the eluent. The title compound was obtained as a yellow oil (0.095 g, 45%); MS (FAB) 311 (M+ +1).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was triturated with dichloromethane
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-b279790288f442a7accbf291ee6677ac
Source dataset
uspto-grants-1999_12
Patent number
US05998414

Reaction notes

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