Hydrogen Bromide → HCID 23361311, compound

HRID 1742250Notes

Reaction equation

HRID 1742250 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:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:7][CH:8]=1.Br.C(=O)(O)[O-].[Na+]>>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][N:10]2[CH2:11][CH2:12][CH2:13][CH:9]2[C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH:16]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 23361296HCID 23361296, compound

Product 1

HCID 23361311HCID 23361311, compoundYield 63%

Procedure

2-(3-Methoxyphenyl)-1-(3-pyridinylmethyl)pyrrolidine and 48% hydrobromic acid (35 ml) were warmed to 100° C. for 7 hrs. The reaction mixture was cooled to ambient temperature, neutralized with saturated sodium bicarbonate solution, and 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 2.2 g (63%) of product, mp 129°-131° C.

Workup

  1. extractionextracted 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-44b2401ab77348b28ff0b5eb1206c6f3
Source dataset
uspto-grants-1994_08
Patent number
US05338739

Reaction notes

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