Sodium Bicarbonate → 3-[1-(2-Pyridinylmethyl)-2-pyrrolidinyl]phenol

HRID 1742247Notes

Reaction equation

HRID 1742247 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:6]=[CH:7][CH:8]=1.C(=O)(O)[O-].[Na+]>Br>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][N:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 233612632-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine

Product 1

HCID 233613143-[1-(2-Pyridinylmethyl)-2-pyrrolidinyl]phenolYield 69%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine and 48% hydrobromic acid (40 ml) were warmed to 100° C. for 7 hrs, cooled to ambient temperature, and neutralized with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane (2 times). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, 1:1 ethyl acetate/dichloromethane). The appropriate fractions were collected and concentrated to give 2.7 g (69%) of product, mp 96°-98° C.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2 times)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, 1:1 ethyl acetate/dichloromethane)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-85002412076e47e7bb66840925fb9310
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

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