HCID 4415129, compound → HCID 67367547, compound

HRID 383984Notes

Reaction equation

HRID 383984 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH2:7][NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1>O>[F:1][C:2]1[CH:18]=[C:17]2[C:5]([CH2:6][CH2:7][N:8]=[C:9]2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 4415129HCID 4415129, compound

Product 1

HCID 67367547HCID 67367547, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 12.5 g (51.4 mmol) of N-(4-fluorophenethyl)benzamide and polyphosphoric acid (150 ml) was heated at 150° C. for 5 days. Then the hot solution was poured into water and the reaction was quenched by the addition of NaHCO3. It was extracted with DCM (3×300 ml). The combined organic phases were washed with brine (300 ml), dried over Na2SO4, filtered and concentrated to small volume under vacuum. 3.2 g of the crude product 7-fluoro-1-phenyl-3,4-dihydroisoquinoline were obtained as the residue, which was reacted further with no additional purification.

Workup

  1. customthe reaction was quenched by the addition of NaHCO3
  2. extractionIt was extracted with DCM (3×300 ml)
  3. washThe combined organic phases were washed with brine (300 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-618f3b3c39a14629b3007f5e1508c08e
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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