1,4-Dimethylpiperazine → HCID 14614944, compound

HRID 1969580Notes

Reaction equation

HRID 1969580 reaction equation
Cl[C:2]1[N:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][N:14]1[CH2:19][CH2:18][N:17](C)[CH2:16][CH2:15]1.C([O-])(O)=O.[Na+].O>O1CCOCC1>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)[N:11]=1

Participants

5

Reactant 3

HCID 78181,4-DimethylpiperazineHCID 2528862,4-DichloroquinazolineHCID 86585896Sodium bicarbonate water

Product 1

HCID 14614944HCID 14614944, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

2,4-Dichloroquinazoline (2.00 g, 10.1 mmol, prepared as described in Prasad, M., et al. Org. Process Res. Dev. 2004, 8, 330-340) was slurried in 1,4-dioxane (20.0 mL). 1,4-Dimethylpiperazine (1.44 mL, 10.6 mmol) was added. The mixture was heated in a CEM microwave at about 150° C. for about 5 min. The material was poured into saturated aqueous NaHCO3/water (1:1, 150 mL). The mixture was extracted with EtOAc (5×100 mL). 20 g of silica gel was added to the combined organics and the volatiles were removed under reduced pressure. The resulting solid was purified by silica gel chromatography eluting with a gradient of 2-10% MeOH/DCM to afford 4-chloro-2-(4-methylpiperazin-1-yl)quinazoline (1.36 g, 52%): LC/MS (Table 1, Method n) Rt=0.51 min; MS m/z 263 (M+H)+.

Workup

  1. extractionThe mixture was extracted with EtOAc (5×100 mL)
  2. addition20 g of silica gel was added to the combined organics and the volatiles
  3. customwere removed under reduced pressure
  4. customThe resulting solid was purified by silica gel chromatography
  5. washeluting with a gradient of 2-10% MeOH/DCM

Sources & evidence

ORD record
ord-8f79e85b7adc4d44bd4cba831cf1335f
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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