Sodium Bicarbonate → HCID 23361300, compound

HRID 233020Notes

Reaction equation

HRID 233020 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>Br.ClCCl>[N:1]1([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 23361270HCID 23361270, compound

Product 1

HCID 23361300HCID 23361300, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 6344DichloromethaneSolvent

Procedure

1-[2-(4-Morpholinyl)ethyl]-2-(3-methoxyphenyl)pyrrolidine (3.6 g) in 48% hydrobromic acid (50 ml) was heated at 100° C. for 8.5 hrs. The reaction mixture was cooled to ambient temperature, neutralized with saturated sodium bicarbonate solution and diluted with dichloromethane. The layers were separated and the aqueous phase was extracted with dichloromethane (3 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 2.0 g (59%) of 3-{1-[2-(4-morpholinyl)ethyl]-2-pyrrolidinyl}phenol.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (3 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-139bee77cd174fc4a6ac5fb0959b926e
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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