Potassium Iodide → 1-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-3-phenyl-2-imidazolidinone, hydrochloride

HRID 369763Notes

Reaction equation

HRID 369763 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.[Cl:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]1=[O:32].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C(C)C>[ClH:17].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][N:23]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:22]4=[O:32])[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 65853EltoprazineHCID 186721151-(3-Chloro-1-propyl)-3-phenyl-2-imidazolidinone

Product 1

HCID 1317206571-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-3-phenyl-2-imidazolidinone, hydrochloride

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 1-(1,4-benzodioxan-5-yl)-piperazine (1.5 g), 1-(3-chloro-1-propyl)-3-phenyl-2-imidazolidinone (1.4 g), potassium carbonate (3 g), and potassium iodide (0.1 g) in methyl isobutyl ketone was refluxed for 20 h. Filtration and removal of solvent in vacuo gave a viscous oil which was separated by column chromatography (silica gel, eluent: ethyl acetate/methanol/triethylamine=15:4:1). The title compound was isolated as an oil which crystallized as the hydrochloride salt from acetone by addition of hydrochloric acid. Yield: 1.9 g, mp: 229-32° C. 1H NMR (δ, DMSO): 1.95-2.15 (m, 2H), 3.00-3.25 (m, 6H), 3.30 (t, 2H), 3.40-3.65 (m, 4H), 3.70-4.00 (m, 4H), 4.15-4.30 (m, 4H), 6.45-6.70 (m, 2H), 6.75 (t, 1H), 7.00 (t, 1H), 7.30 (t, 2H), 7.60 (d, 2H), 11.30 (b, 1H).

Workup

  1. temperaturewas refluxed for 20 h
  2. filtrationFiltration and removal of solvent in vacuo
  3. customgave a viscous oil which
  4. customwas separated by column chromatography (silica gel, eluent: ethyl acetate/methanol/triethylamine=15:4:1)

Sources & evidence

ORD record
ord-2e10c1a561424a4ca60cadb9eaba3e3b
Source dataset
uspto-grants-2000_10
Patent number
US06140331

Reaction notes

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