1-(2-Methoxyphenyl)piperazine → HCID 86745195, compound

HRID 973426Notes

Reaction equation

HRID 973426 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[C:9]2=[N:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:8]2[C:7](=[O:17])[N:6]([CH3:18])[CH2:5]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[C:33]([O-:36])([OH:35])=O.[Na+].CN(C=O)C>O>[C:21]([OH:20])(=[O:17])/[CH:22]=[CH:23]/[C:33]([OH:36])=[O:35].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH:4]2[C:9]3=[N:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:8]3[C:7](=[O:17])[N:6]([CH3:18])[CH2:5]2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 199898454-(2-Chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one

Product 1

HCID 86745195HCID 86745195, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g (0.015 mol) of 4-(2-chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazole-1(2H)-one, 2.93 g (0.015 mol) of 1-(2-methoxyphenyl)piperazine, 9 g of NaHCO3, 0.5 g of Kl, and 30 mL of DMF was heated on a steam cone for 18 h. The reaction mixture was poured into 400 mL of H2O and extracted with 2×100 mL CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated by rotary evaporation. The resulting oil was purified by preparative HPLC eluting with acetone and using silica gel as the stationary phase. Like fractions were combined and concentrated by rotary evaporation to an oil. The oil was treated with fumaric acid in 2-propanol to give 3.7 g (42%) of the salt, mp 100°-108° C. dec.

Workup

  1. temperaturewas heated on a steam cone for 18 h
  2. extractionextracted with 2×100 mL CH2Cl2
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe resulting oil was purified by preparative HPLC
  7. washeluting with acetone
  8. concentrationconcentrated by rotary evaporation to an oil
  9. additionThe oil was treated with fumaric acid in 2-propanol

Sources & evidence

ORD record
ord-19e9ef3df95b4c999008f407ba6c7c6a
Source dataset
uspto-grants-1991_11
Patent number
US05063228

Reaction notes

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