4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazole → 3-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]-1-propanamine

HRID 353081Notes

Reaction equation

HRID 353081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:5][C:6]1[C:7]([CH2:13][CH3:14])=[N:8][NH:9][C:10]=1[CH2:11][CH3:12].Cl.Cl[CH2:21][CH2:22][CH2:23][NH2:24]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[CH2:5][C:6]1[C:10]([CH2:11][CH3:12])=[N:9][N:8]([CH2:21][CH2:22][CH2:23][NH2:24])[C:7]=1[CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 98569994-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazoleHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 101320193-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]-1-propanamineYield 84%

Conditions

Temperature
150 °C

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.

Workup

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

Sources & evidence

ORD record
ord-f5cc3f84fe18451fa3d3968232769bab
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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