Potassium Hydroxide → HCID 59536346, compound

HRID 445364Notes

Reaction equation

HRID 445364 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][CH2:6][NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:4]=1[CH2:5][CH2:6][N:7]=[C:8]2[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 17429727N-(2-methoxyphenethyl)-4-(trifluoromethyl)benzamide

Product 1

HCID 59536346HCID 59536346, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 100 mL round-bottomed flask was added N-(2-methoxyphenethyl)-4-(trifluoromethyl)benzamide (1.41 g, 4361 μmol, from step 1), toluene (30 mL), phosphorus pentoxide (1077 μL, 17445 μmol, Aldrich). The reaction mixture was stirred at reflux for overnight (ca 18 h). The mixture was cooled down to RT and poured it to ice (ca 100 g). The mixture was neutralized with KOH until pH 12. The mixture was extracted with EtOAc (2×100 mL). The organic extract was washed with saturated NaCl (50 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give 5-methoxy-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline. MS (ESI pos. ion) m/z: 306 (M+1).

Workup

  1. temperatureat reflux for overnight (ca 18 h)
  2. extractionThe mixture was extracted with EtOAc (2×100 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-da5eb57118824ec4a6d3f98ab49fa7f2
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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