Hydrogen Bromide → HCID 13925234, compound

HRID 501215Notes

Reaction equation

HRID 501215 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2OC)[C:10](=[O:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.[OH-].[NH4+]>C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:22][C:10]=2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 13925233HCID 13925233, compound

Product 1

HCID 13925234HCID 13925234, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The crude 1-benzyl-4-(2-methoxyphenyl)piperidin-3-one (0.7 g, 2.37 mmol) obtained in the previous step was dissolved in 4 mL of glacial acetic acid. To this solution, 48% hydrobromic acid (4 mL) was added, and the mixture was refluxed under N2 for 4 h. After cooling to room temperature, the reaction mixture was poured over ice cold ethyl acetate (50 mL) and concentrated ammonium hydroxide solution (50 mL). The organic phase was washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 2-benzyl-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine (200 mg, 33%). 1H NMR (200 MHz, CDCl3): δ 2.70-2.76 (m, 2H) 2.85-2.91 (m, 2H), 3.67 (t, J=1.8 Hz, 2H), 3.78 (s, 2H), 7.18-7.45 (m, 9H); m/e=263 (M+).

Workup

  1. temperaturethe mixture was refluxed under N2 for 4 h
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5d80ddd2b2aa4253a41df829dbb59ee9
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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