Reaction #810787

Reaction equation

pyrazole

4-(3,5-Dichlorobenzyl)-3,5-diethyl-1H-pyrazole

3-chloropropylamine hydrochloride

→

title compound

Yield 84.0%

3-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1H-pyrazol-1-yl]-1-propanamine

Yield 84.0%

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Otherthe reaction mixture was partitioned between dichloromethane (30 ml) and saturated aqueous sodium hydrogencarbonate solution (30 ml)
3. 3
   DryingThe organic phase was dried over anhydrous magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (90:10:0, by volume)

Procedure

The pyrazole of Example 11 (200 mg, 0.71 mmol) was mixed with 3-chloropropylamine hydrochloride (138 mg, 1.06 mmol). The resulting mixture was heated neat at 150° C., for 24 hours, under a nitrogen atmosphere. After cooling, the reaction mixture was partitioned between dichloromethane (30 ml) and saturated aqueous sodium hydrogencarbonate solution (30 ml). The organic phase was dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (90:10:0, by volume) gradually changing to dichloromethane:methanol:ammonia (90:10:1, by volume) to afford the title compound (203 mg) as a brown oil.

Source