Hydrogen Bromide → HCID 24750602, compound

HRID 339656Notes

Reaction equation

HRID 339656 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22]C)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([O:17]C)[CH:10]=1.Br.C(=O)([O-])O.[Na+]>O>[OH:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[OH:22])[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:17])[CH:10]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 714966HCID 714966, compound

Product 1

HCID 24750602HCID 24750602, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

The crude bis(3,4-dimethoxybenzyl)amine (0.6 g) was combined with hydrobromic acid (6 ml of 48% w/w solution in water) and slowly heated with stirring, to 145° C. over 1 h. The reaction was maintained at 145° C. for 12 h, allowed to cool to room temperature, and poured into water (25 ml). The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate (25 ml). The organic layer was washed into water (2×25 ml), dried (Na2SO4) and the solvent removed under reduced pressure to afford DC-0073 as a solid, 160 mg.

Workup

  1. temperatureslowly heated
  2. temperatureThe reaction was maintained at 145° C. for 12 h
  3. temperatureto cool to room temperature
  4. extractionextracted with ethyl acetate (25 ml)
  5. washThe organic layer was washed into water (2×25 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed under reduced pressure
  8. customto afford DC-0073 as a solid, 160 mg

Sources & evidence

ORD record
ord-24d445d33be6489e9258febf3fc360c3
Source dataset
uspto-grants-2014_11
Patent number
US08895554B2

Reaction notes

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