4-(4-Benzylpiperazin-1-yl)-6-chloropyrimidine → 4-(Piperazin-1-yl)pyrimidine

HRID 2288742Notes

Reaction equation

HRID 2288742 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][N:17]=[C:16](Cl)[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[N:17]1[CH:16]=[CH:15][C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:19][CH:18]=1

Participants

4

Reactant 1

HCID 186980524-(4-Benzylpiperazin-1-yl)-6-chloropyrimidine

Product 1

HCID 183211374-(Piperazin-1-yl)pyrimidineYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(Benzyl)-4-(4-chloropyrimidin-6-yl)piperazine (58.0 g; 0.20 mol) was dissolved, with some heating, in methanol (700 ml), treated with 10% Pd on activated carbon (11.6 g) and agitated and hydrogenated at s.t.p. for 8 h. After this period the catalyst was removed by filtering through celite. The filtrate thus obtained was then evaporated under reduced pressure to a yellow-brown viscous gum which was chromatographed through 60 μm silica gel, eluting with 5% methanol, 1% ammonium hydroxide and 94% CH2Cl2 to obtain as white solid, 25 g (76% yield based on prehydrogenation substrate) of 4-(4-pyrimidinyl)piperazine;

Workup

  1. customAfter this period the catalyst was removed
  2. filtrationby filtering through celite
  3. customThe filtrate thus obtained
  4. customwas then evaporated under reduced pressure to a yellow-brown viscous gum which
  5. customwas chromatographed through 60 μm silica gel
  6. washeluting with 5% methanol, 1% ammonium hydroxide and 94% CH2Cl2

Sources & evidence

ORD record
ord-9fb5c09c309b44429f777930c7e21272
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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