Sodium Bicarbonate → HCID 22038115, compound

HRID 1790401Notes

Reaction equation

HRID 1790401 reaction equation
C[O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[CH2:13][CH2:14]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22038321HCID 22038321, compound

Product 1

HCID 22038115HCID 22038115, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1-[1-(4-Methoxyphenethyl)piperidin-4-yl]indoline (0.23 g) was dissolved in a 47% aqueous solution (5 ml) of hydrobromic acid and the resultant solution was heated under reflux for 90 min. After allowing to cool, the resultant mixture was poured into a saturated aqueous solution of sodium bicarbonate (pH 9-10), extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (0.113 g) as colorless crystals (yield: 75.7%).

Workup

  1. temperatureunder reflux for 90 min
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-2fc0163eedf04b9084ed4dbc0ab44981
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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