Trifluoroacetic acid → HCID 11369085, compound

HRID 639885Notes

Reaction equation

HRID 639885 reaction equation
[Cl-].COC1C=C(C=CC=1OC)C[NH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]([CH3:27])[NH+:10]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:20][O:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[C:9]([NH2:8])=[N:10][C:11]([CH3:27])=[C:12]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68517325HCID 68517325, compound

Product 1

HCID 11369085HCID 11369085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The free base of 1-[(3,4-dimethoxybenzyl)amino]-6-methoxy-3-methyl-4-phenylisoquinolinium chloride was treated with 5 mL of CH2Cl2 and 10 mL of trifluoroacetic acid. The reaction was stirred at room temp for 2 h, then concentrated to dryness. The residue was combined with saturated aqueous sodium carbonate, and the mixture was extracted with EtOAc (3×). The combined organic solutions were dried (Na2SO4) and concentrated. Recrystallization from EtOAc/hexanes gave a solid which was further purified by flash chromatography (0-1% MeOH/ammonia-saturated CHCl3). The solid thus obtained was triturated with hexanes to give the titled compound.

Workup

  1. concentrationconcentrated to dryness
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. dry with materialThe combined organic solutions were dried (Na2SO4)
  4. concentrationconcentrated
  5. customRecrystallization from EtOAc/hexanes
  6. customgave a solid which
  7. customwas further purified by flash chromatography (0-1% MeOH/ammonia-saturated CHCl3)
  8. customThe solid thus obtained
  9. customwas triturated with hexanes

Sources & evidence

ORD record
ord-52cee1e8ee88448f94d19f05b77b7d07
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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