Hydrogen Bromide → HCID 10381970, compound

HRID 2170275Notes

Reaction equation

HRID 2170275 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27]C)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([O:22]C)[CH:15]=2)[CH2:9][CH2:8]1.Br.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O>[OH:22][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[OH:20])[CH2:13][N:10]1[CH2:9][CH2:8][N:7]([CH2:6][C:5]2[CH:24]=[CH:25][C:26]([OH:27])=[C:3]([OH:2])[CH:4]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 1074708HCID 1074708, compound

Product 1

HCID 10381970HCID 10381970, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

1,4-Bis(3,4-dimethoxybenzyl)piperazine (5 g, 12.95 mmol) was combined with hydrobromic acid (50 ml of 48% w/w solution in water) and the solution heated slowly over 1 hour to 145° C. Reaction was maintained at 145° C. for 12 h at which time TLC revealed disappearance of starting material. The cooled solution was diluted with water (200 ml), carefully neutralized with saturated aqueous sodium hydrogen carbonate, and ethyl acetate (100 ml) added. The crude aqueous solvent mixture was filtered through Celite and the ethyl acetate layer separated. The aqueous layer was extracted with ethyl acetate (2×50 ml), and the combined extracts washed with water (50 ml), and dried (Na2SO4). The solvent was removed under reduced pressure and the residue recrystallized from toluene and methyl ethyl ketone to afford the product, DC-0009, 100 mg (98%, pure by HPLC analysis).

Workup

  1. temperaturethe solution heated slowly over 1 hour to 145° C
  2. customReaction
  3. additionadded
  4. filtrationThe crude aqueous solvent mixture was filtered through Celite
  5. customthe ethyl acetate layer separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  7. washthe combined extracts washed with water (50 ml)
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was removed under reduced pressure
  10. customthe residue recrystallized from toluene and methyl ethyl ketone
  11. customto afford the product, DC-0009, 100 mg (98%, pure by HPLC analysis)

Sources & evidence

ORD record
ord-72c8b4cb32574663bada54ea401ae7b6
Source dataset
uspto-grants-2015_06
Patent number
US09051253B2

Reaction notes

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