Piperazine → 4,6-Dichloro-2-(piperazin-1-yl)pyrimidine

HRID 1721286Notes

Reaction equation

HRID 1721286 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>O1CCCC1>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[N:3]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 215170134,6-Dichloro-2-(piperazin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.56 ml (4.87 mmoles) of 2,4,6-trichloropyrimidine diluted with 20 ml of tetrahydrofuran is dropwise added to a solution of 2.0 g (5.12 mmoles) of 1- (3α,16α)-eburnamenine-14-carbonyl!piperazine in 50 ml of tetrahydrofuran at 0° C. After stirring at room temperature for 12 hours the reaction mixture is evaporated to dryness. The residue is distributed between 100 ml of chloroform and 25 ml of 5% sodium hydroxide solution. After separation the organic phase is dried, evaporated and the evaporation residue is subjected to chromatography on silica gel column. By using a chloroform/methanol mixture (100:0→99:1) as eluent, the less polar 1- (3α,16α)-eburnamenine-14-carbonyl!-4-(4,6-dichloro-2-pyrimidinyl)piperazine is first obtained in a yield of 0.325 g (12.7%), m.p.: 100°-107° C. (after recrystallization from ether). By further elution the more polar 1- (3α,16α)-eburnamenine-14-carbonyl!-4-(2,4-dichloro-6-pyrimidinyl)piperazine is obtained in a yield of 2.26 g (88.3%), m.p.: 165°-175° C. (after recrystallization from ether).

Workup

  1. additionis dropwise added to a solution of 2.0 g (5.12 mmoles) of 1- (3α,16α)-eburnamenine-14-carbonyl
  2. customat 0° C
  3. customis evaporated to dryness
  4. customAfter separation the organic phase
  5. customis dried
  6. customevaporated

Sources & evidence

ORD record
ord-3db0c648e8be4cf38b8483ba7c026f88
Source dataset
uspto-grants-1996_04
Patent number
US05510345

Reaction notes

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