Acetic Acid → HCID 22037913, compound

HRID 1790487Notes

Reaction equation

HRID 1790487 reaction equation
Br.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[C:26]4[C:21](=[CH:22][C:23]([O:27]C)=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.C(O)(=O)C>O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[C:26]4[C:21](=[CH:22][C:23]([OH:27])=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 22038088HCID 22038088, compound

Product 1

HCID 22037913HCID 22037913, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

47% hydrobromic acid (45 ml) was added to 1-[2-(4-fluorophenyl)ethyl]-4-(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)piperidine (2.718 g, 7.57 mmol) and the resultant mixture was heated under reflux for 1 hr. After adding glacial acetic acid (20 ml), the resultant mixture was heated under reflux for additional 1.5 hr. Then the mixture was allowed to cool followed by addition of water thereto. The resulting precipitate was collected by filtration, chloroform and a saturated aqueous solution of sodium bicarbonate were added thereto and the layers were separated. The resulting solution was dried over magnesium sulfate and the solvent was evaporated under reduced pressure to give the title compound (2.043 g) as a brown amorphous substance (yield: 76.4%).

Workup

  1. temperatureunder reflux for 1 hr
  2. temperatureunder reflux for additional 1.5 hr
  3. temperatureto cool
  4. filtrationThe resulting precipitate was collected by filtration, chloroform
  5. additiona saturated aqueous solution of sodium bicarbonate were added
  6. customthe layers were separated
  7. dry with materialThe resulting solution was dried over magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d653e8801eb0417599bfb129e924602d
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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