Hydrochloric Acid → 1-[4-(7-Phenyl-3,4-dihydronaphthalene-2-carboxamido)-benzyl]pyridinium chloride

HRID 565869Notes

Reaction equation

HRID 565869 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:18]=3)[CH:13]=2)=[O:11])=[CH:5][CH:4]=1.C([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C.[CH3:35]S(OS(C)(=O)=O)(=O)=O.[ClH:44]>C1COCC1>[Cl-:44].[C:22]1([C:16]2[CH:15]=[C:14]3[C:19]([CH2:20][CH2:21][C:12]([C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([CH2:2][N+:30]5[CH:31]=[CH:32][CH:35]=[CH:34][CH:33]=5)=[CH:8][CH:7]=4)=[O:11])=[CH:13]3)=[CH:18][CH:17]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 10641929N-[4-(hydroxymethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide

Product 1

HCID 184726661-[4-(7-Phenyl-3,4-dihydronaphthalene-2-carboxamido)-benzyl]pyridinium chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-[4-(hydroxymethyl)phenyl]-7-phenyl-3,4-dihydronaphthalene-2-carboxamide (200mg), triethylamine (158 μl) and THF (10ml) was added methane-sulfonic acid anhydride (118mg) at 0° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF (3ml), and to the mixture was added pyridine (137 μl). The mixture was stirred at room temperature for 96 hours and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-methanol to give 1-[4-(7-phenyl-3,4-dihydronaphthalene-2-carboxamido)-benzyl]pyridinium chloride (Compound 18) (95mg) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DMF (3ml)
  6. additionto the mixture was added pyridine (137 μl)
  7. stirringThe mixture was stirred at room temperature for 96 hours
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-dfad73c8c37d4f5a835078615f230cc1
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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