2-Chloroethylamine hydrochloride → HCID 10268315, compound

HRID 558262Notes

Reaction equation

HRID 558262 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O: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)[O: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 9878953HCID 9878953, compound

Product 1

HCID 10268315HCID 10268315, compoundYield 54.3%

Conditions

Temperature
150 °C

Procedure

A mixture of the pyrazole (390 mg, 1.37 mmol) of Example 3 and chloroethylamine hydrochloride (238 mg, 2.05 mmol) was stirred and heated at 150° C. for 24 hours. After cooling, the mixture was partitioned between saturated aqueous sodium bicarbonate solution (100 ml) and dichloromethane (2×50 ml). The combined organic layers were washed with brine (30 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting brown oil was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (90:10, by volume) to afford the title compound (244 mg) as a brown oil.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between saturated aqueous sodium bicarbonate solution (100 ml) and dichloromethane (2×50 ml)
  3. washThe combined organic layers were washed with brine (30 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting brown oil was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (90:10, by volume)

Sources & evidence

ORD record
ord-3787c67a4cec4b3f95049e7107f7c844
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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