1-Methylpiperazine → HCID 3252419, compound

HRID 2209880Notes

Reaction equation

HRID 2209880 reaction equation
Cl[C:2]1[C:3]([Cl:9])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(O)C>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:5]2[N:6]=[C:7]([N:14]3[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]3)[CH:2]=[C:3]([Cl:9])[N:4]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 3252419HCID 3252419, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trichloropyrimidine is added in portions to an ice cool solution of N-methylpiperazine (40 g) in ethanol (200 ml). The mixture is then heated at 60° for 2 h. The mixture is concentrated and chromatographed on silica gel with 2-5% methanol and methylene chloride to give 2,4-bis[4-methylpiperazino]-6-chloropyrimidine. This material is heated at 130° in water (30 ml) with piperazine (32 g) in a Parr bomb for 20 h. The product is partitioned between methylene chloride and aqueous sodium carbonate. The phases are separated and the organic phase is dried over sodium sulfate and concentrated to give the title compound, TLC (methylene chloride/methanol/ammonium hydroxide -91.5/8/0.5) Rf =0.3.

Workup

  1. temperatureThe mixture is then heated at 60° for 2 h
  2. concentrationThe mixture is concentrated
  3. customchromatographed on silica gel with 2-5% methanol and methylene chloride

Sources & evidence

ORD record
ord-58e7c45a343844f6bc2e874286eba290
Source dataset
uspto-grants-1995_10
Patent number
USRE035053

Reaction notes

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