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

HRID 1710080Notes

Reaction equation

HRID 1710080 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-efc8c98e0e5c40aabdb76d1c2f0cd7c6
Source dataset
uspto-grants-1990_08
Patent number
US04952589

Reaction notes

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