1-(2-Methoxyphenyl)piperazine → HCID 10874021, compound

HRID 342561Notes

Reaction equation

HRID 342561 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[N:10]([CH2:16][CH2:17][CH2:18]Cl)[C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C(#N)C>[CH2:1]([N:8]1[CH:13]=[C:12]([CH3:14])[C:11](=[O:15])[N:10]([CH2:16][CH2:17][CH2:18][N:32]2[CH2:31][CH2:30][N:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][CH3:21])[CH2:34][CH2:33]2)[C:9]1=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 111199111-benzyl-3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 10874021HCID 10874021, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-benzyl-3-(3-chloropropyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (550 mg, 1.87 mmol), prepared as in Example 19, 1-(2-methoxyphenyl)piperazine (367 g, 1.87 mmol), sodium iodide (623 g, 3.75 mmol), potassium carbonate (260 mg, 1.81 mmol) and acetonitrile (50 mL) was stirred 8 hours at reflux. The reaction mixture then was poured into water (200 mL) and extracted with methylene chloride (3×100 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to give 1-benzyl-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-5-methyl-2,4(1H,3H)-pyrimidinedione (800 mg, 1.78 mmol) as an oil. The free base was recrystallized from a solution of hydrochloric acid in alcohol to give 1-benzyl-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propy1}-5-methyl-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 195°-198° C. Anal.: Calcd. for C26H32N4O3.(HCl)2 : C, 59.88; H, 6.57; N, 10.74%; Found: C, 59.71; H, 6.64; N, 10.73%.

Workup

  1. temperatureat reflux
  2. extractionextracted with methylene chloride (3×100 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-b7da5036c7a9460caa3b29f250707cda
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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