2-Bromo-3-methoxypyridine → HCID 23035473, compound

HRID 2118978Notes

Reaction equation

HRID 2118978 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:20]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][N:21]=1>>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH:15][C:20]2[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 903642-Bromo-3-methoxypyridineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 23035473HCID 23035473, compound

Conditions

Temperature
100 °C

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (3.97 g) and 2-bromo-3-methoxypyridine (1.50 g) were heated with stirring at 100° C. for 48 hours. The cooled residue was partitioned between chloroform and water. The aqueous layer was further extracted with chloroform and the combined chloroform layers were washed with water, dried and evaporated to dryness. The brown residue was dissolved in aqueous acetic acid to pH 4 and extracted with ether to remove unreacted 2-bromo-3-methoxypyridine. The aqueous solution was basified with potassium carbonate to pH 9-10 and then extracted with chloroform. The combined chloroform extracts were washed, dried and evaporated to dryness. The residue was subjected to column chromatography on silica with chloroform as eluant to afford the title compound as an oil. This was treated with maleic acid in isopropanol to give as a white solid, 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-3-methoxypyridine dimaleate (0.82 g), m.p. 111°-112° C. (recrystallised from acetone-ethyl acetate).

Workup

  1. customThe cooled residue was partitioned between chloroform and water
  2. extractionThe aqueous layer was further extracted with chloroform
  3. washthe combined chloroform layers were washed with water
  4. customdried
  5. customevaporated to dryness
  6. dissolutionThe brown residue was dissolved in aqueous acetic acid to pH 4
  7. extractionextracted with ether
  8. customto remove unreacted 2-bromo-3-methoxypyridine
  9. extractionextracted with chloroform
  10. washThe combined chloroform extracts were washed
  11. customdried
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-7f53e7a6bee24d38a496a12dced4feb6
Source dataset
uspto-grants-1987_07
Patent number
US04681883

Reaction notes

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