2-Chloroethylamine hydrochloride → HCID 9966018, compound

HRID 353072Notes

Reaction equation

HRID 353072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[CH2:5][C:6]1[C:7]([CH3:12])=[N:8][NH:9][C:10]=1[CH3:11].Cl.Cl[CH2:19][CH2:20][NH2:21]>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[CH2:5][C:6]1[C:10]([CH3:11])=[N:9][N:8]([CH2:19][CH2:20][NH2:21])[C:7]=1[CH3:12]

Participants

5

Reactant 2

HCID 97937372-Chloroethylamine hydrochlorideHCID 9834883HCID 9834883, compound

Product 1

HCID 9966018HCID 9966018, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A stirred suspension of the pyrazole (200 mg, 0.78 mmol) of Example 23 and 2-chloroethylamine hydrochloride (136 mg, 1.18 mmol) in toluene (1 ml) was heated at 120° C. in a sealed Reacti-vial (Trade Mark) for 18 hours. After cooling, the mixture was diluted with dichloromethane (30 ml), washed with 2 M aqueous sodium hydroxide solution (20 ml), dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with methanol:dichloromethane:ammonia (5:95:0.5, by volume) to afford the title compound (45 mg) as white crystals, m.p. 70-72° C.

Workup

  1. temperatureAfter cooling
  2. washwashed with 2 M aqueous sodium hydroxide solution (20 ml)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel eluting with methanol:dichloromethane:ammonia (5:95:0.5, by volume)

Sources & evidence

ORD record
ord-4edc0b0e77b643209faf665a57822ce1
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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