Phenethylamine → HCID 23555693, compound

HRID 1635498Notes

Reaction equation

HRID 1635498 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH2:20]([NH2:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[C:22]1([CH2:21][CH2:20][NH:28][C:2]2[CH:7]=[C:6]([C:8]3[N:12]([C:13]4[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=4)[N:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 18676092HCID 18676092, compound

Product 1

HCID 23555693HCID 23555693, compoundYield 70%

Conditions

Temperature
190 °C

Procedure

A mixture of 2-chloro-4-[1-(4-fluorophenyl)-1H-pyrazol-5-yl]pyridine (Example 46; 0.6 g, 0.002 mol) and phenethylamine (20 mL) was heated at 190° C. for 24 hours. The excess amine was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8) to give 0.55 g (70% yield) of product as a yellow oil: Anal. Calc'd. for C22H19FN4: C, 73.72; H, 5.34; N, 15.63. Found: C, 73.33; H, 5.46; N, 15.22.

Workup

  1. customThe excess amine was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8)

Sources & evidence

ORD record
ord-328f72f6f3cc4382b35bee2f02fd3e61
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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