1-Methylpiperazine → HCID 18381682, compound

HRID 2297461Notes

Reaction equation

HRID 2297461 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH2:14][C:15]2[C:20]([Cl:21])=[CH:19][N:18]=[CH:17][C:16]=2[Cl:22])=[N:4][N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>CN(C=O)C>[Cl:22][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([Cl:21])[C:15]=1[CH2:14][C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[C:2]([N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[N:3][N:4]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 186292104-Chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine

Product 1

HCID 18381682HCID 18381682, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (1 g, 2.82 mmoles), prepared as described in example 45, in DMF (25 ml) was stirred under dry N2 at room temperature, and dropwise added with 1-methylpiperazine (0.848 g, 8.46 mmoles). The mixture was heated at 100° C. for 20 hours, then brought to small volume and partitioned between water and CH2Cl2. The organic phase was washed with water, anhydrified and concentrated to give a residue which was flash chromatographed (eluent: CH2Cl2/CH3OH/NH4OH 95:5:0.5). The resultant solid was crystallised from tert-butyl-methyl ether (35 ml) to give 0.4 g of the title compound (yield: 34%). m.p.: 160-162° C.

Workup

  1. temperatureThe mixture was heated at 100° C. for 20 hours
  2. custompartitioned between water and CH2Cl2
  3. washThe organic phase was washed with water, anhydrified
  4. concentrationconcentrated
  5. customto give a residue which
  6. customchromatographed (eluent: CH2Cl2/CH3OH/NH4OH 95:5:0.5)
  7. customThe resultant solid was crystallised from tert-butyl-methyl ether (35 ml)

Sources & evidence

ORD record
ord-22e4f0e634944cbb852c023c0130c111
Source dataset
uspto-grants-2002_12
Patent number
US06492360B1

Reaction notes

Loading…