1-(2-Methoxyphenyl)piperazine → HCID 21473675, compound

HRID 2294030Notes

Reaction equation

HRID 2294030 reaction equation
Br.Br.Br[CH2:4][C:5]1[C:6]([NH2:14])=[N:7][C:8]([CH2:11][CH2:12][CH3:13])=[N:9][CH:10]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][N:26]([CH2:4][C:5]2[C:6]([NH2:14])=[N:7][C:8]([CH2:11][CH2:12][CH3:13])=[N:9][CH:10]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 11430Potassium CarbonateHCID 21473668HCID 21473668, compound

Product 1

HCID 21473675HCID 21473675, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 7.0 g (0.020 mol) of 5-bromomethyl-2-propyl-pyrimidin-4-ylamine dihydrobromide, 3.85 g (0.020 mol) of (2-methoxy-phenyl)-piperazine and 6 g (0.043 mol) of dry potassium carbonate in 75 ml of dimethylformamide was dissolved at room temperature for 4 hours. The reaction mixture was suction filtered, the filter cake was washed with ethyl acetate and ethanol, the filtrate was completely freed from the solvents and the residue was chromatographed over silica gel with ethyl acetate as the eluent and recrystallized from hot ethyl acetate. 1.3 g (21%) of 5-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]-2-propyl-pyrimidin-4-ylamine were obtained as yellowish crystals, m.p. 130°.

Workup

  1. dissolutionwas dissolved at room temperature for 4 hours
  2. filtrationfiltered
  3. washthe filter cake was washed with ethyl acetate and ethanol
  4. customthe residue was chromatographed over silica gel with ethyl acetate as the eluent
  5. customrecrystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-1cf885c9b94741c69ec69a32278410c1
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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