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

HRID 723605Notes

Reaction equation

HRID 723605 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-283d2ad3b5744a299d56ce5c7e6a4d71
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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