Sodium Bicarbonate → HCID 23361300, compound

HRID 742565Notes

Reaction equation

HRID 742565 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-5fefbdb84bda4e28965f681ee86b861c
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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