Hydrochloric Acid → HCID 61237299, compound

HRID 2251526Notes

Reaction equation

HRID 2251526 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[NH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(OCC)(=O)C.Cl>O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5610TyramineHCID 8857Ethyl AcetateHCID 693532,5-Dibromopyridine

Product 1

HCID 61237299HCID 61237299, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,5-dibromo-pyridine (5 g; 21.10 mmol) and tyramine (5.79 g; 42.21 mmol) was heated at 200C for 1 hour. Upon cooling the residue was taken up into ethyl acetate, water and 1N HCl. The phases were separated and the organic phase was washed twice with 1N HCl. The combined aqueous phases were basified to pH-9 with 2N NaOH and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to afford 4-{2-[(5-bromopyridin-2-yl)amino]ethyl}phenol as a beige solid (5 g; 80% yield), which was used in the next step without further purification.

Workup

  1. temperatureUpon cooling the residue
  2. customThe phases were separated
  3. washthe organic phase was washed twice with 1N HCl
  4. extractionextracted twice with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9da5d257848b4cf69f45b9256b77b89e
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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