2,3-Dichloropyridine → HCID 23035490, compound

HRID 2118963Notes

Reaction equation

HRID 2118963 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.Cl[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=1>CC1C=NC=CC=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]([Cl:26])=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 169882,3-DichloropyridineHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 23035490HCID 23035490, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 79703-MethylpyridineSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (2.17 g) and 2,3-dichloropyridine (1.27 g) were dissolved in 3-methylpyridine (6 ml) and stirred under reflux for 16 hours. The majority of the reaction solvent was removed by vacuum distillation (120 torr, 70°-80° C.) and the residue was neutralised with aqueous potassium carbonate (5%; 40 ml), washed with water (2×100 ml) and extracted into chloroform (40 ml). The chloroform extract was evaporated under reduced pressure and subjected to column chromatography (chloroform:methanol 25:1) to give the title compound as an oil (1.15 g). This was treated with oxalic acid as in Example 1 to give 2-[3-[3-(piperidinomethyl)phenoxy]propylamino]-3-chloropyridine dioxalate (1.1 g), m.p. 154°-155° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe majority of the reaction solvent was removed by vacuum distillation (120 torr, 70°-80° C.)
  3. washwashed with water (2×100 ml)
  4. extractionextracted into chloroform (40 ml)
  5. extractionThe chloroform extract
  6. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-13331dcc44064ab0b913af41985907d4
Source dataset
uspto-grants-1987_07
Patent number
US04681883

Reaction notes

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