1-Phenethylamine, (-)- → HCID 90414004, compound

HRID 1521941Notes

Reaction equation

HRID 1521941 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[C:9]1([C@@H:15]([NH2:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:17][C@H:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:16])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 6394382-Bromo-6-fluoropyridine

Product 1

HCID 90414004HCID 90414004, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-6-fluoropyridine (500 mg, 2.84 mmol) and (S)-(−)-1-phenylethylamine (0.435 mL, 3.41 mmol) were heated at 100° C. for 12 hours. The mixture was cooled to room temperature, dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 6% ethyl acetate-hexane) afforded the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (silica gel, 6% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c0bc0370de2e49e7901017f07b8ebbc0
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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