2-Chloroethylamine hydrochloride → 2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethanamine

HRID 723600Notes

Reaction equation

HRID 723600 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][NH2:23]>>[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][NH2:23])[C:7]=1[CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 97937372-Chloroethylamine hydrochlorideHCID 98569994-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazole

Product 1

HCID 99233572-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethanamineYield 53.5%

Conditions

Temperature
150 °C

Procedure

The pyrazole of Example 11 (5.47 g, 19.3 mmol) was mixed with 2-chloroethylamine hydrochloride (2.46 g, 21.3 mmol) and heated neat at 150° C. for 20 hours. After cooling, the solid was partitioned between dichloromethane and 10% aqueous potassium carbonate solution. The organic extract was concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0, by volume) gradually changing to dichloromethane:methanol:ammonia (90:10:1, by volume) to afford the title compound (3.37 g) as a colourless oil.

Workup

  1. temperatureAfter cooling
  2. customthe solid was partitioned between dichloromethane and 10% aqueous potassium carbonate solution
  3. extractionThe organic extract
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude material was purified by flash chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0, by volume)

Sources & evidence

ORD record
ord-66615fd9586841e3a83af1882f4c1e7e
Source dataset
uspto-grants-2006_11
Patent number
US07141585B2

Reaction notes

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