2-Bromo-6-methoxypyridine → HCID 23035486, compound

HRID 2118968Notes

Reaction equation

HRID 2118968 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[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=1>Cl>[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[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2568102-Bromo-6-methoxypyridineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 23035486HCID 23035486, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (14.90 g) and 2-bromo-6-methoxypyridine (5.64 g) were heated with stirring in an oil bath at 165°-170° C. for 5 hours. The reaction mixture was cooled, dissolved in dilute hydrochloric acid to pH 3-4, washed with ether (5 times), taken to pH 9-10 with dilute sodium hydroxide, extracted into ether (5 times). The pH was adjusted after each extraction. The latter ether extracts were combined, dried (MgSO4), evaporated under reduced pressure, and subjected to medium pressure chromatography on silica using ethyl acetate as eluant, to yield the title compound as an oil (2.45 g). This was treated with maleic acid in ethanol to give 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-6-methoxypyridine dimaleate (2.71 g), m.p. 114.5°-115° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with ether (5 times)
  3. extractionextracted into ether (5 times)
  4. extractionafter each extraction
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-aab9bb208052437db4a243970d118f3e
Source dataset
uspto-grants-1987_07
Patent number
US04681883

Reaction notes

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