Sodium Bicarbonate → HCID 15291371, compound

HRID 233018Notes

Reaction equation

HRID 233018 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[N:13]([CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:12](=[O:22])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]2[N:13]([CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[C:12](=[O:22])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23361277HCID 23361277, compound

Product 1

HCID 15291371HCID 15291371, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

5-(3-Methoxyphenyl)-1-[2-(4-morpholinyl)ethyl]-2-pyrrolidinone (12.8 g) was dissolved in 48% hydrobromic acid (100 ml) and warmed at 100° C. for 4.5 hrs. The reaction mixture was cooled to ambient temperature, neutralized with saturated sodium bicarbonate solution, and the mixture was extracted with dichloromethane (6 times). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, ether). The appropriate fractions were collected and concentrated to give 3.3 g (55%) of 5-(3-hydroxyphenyl)-1-[2-(4-morpholinyl)ethyl]-2-pyrrolidinone.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionthe mixture was extracted with dichloromethane (6 times)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash column chromatography (silica gel, ether)
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1c4d905f3cf2485bb2a745fa4a3584d2
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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