Ammonium Chloride → HCID 20295596, compound

HRID 1389871Notes

Reaction equation

HRID 1389871 reaction equation
[Mg].Br[C:3]1[C:12]([O:13][CH2:14][CH3:15])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[Cl:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1.[Cl-].[NH4+].[H][H]>O1CCCC1>[ClH:16].[CH2:14]([O:13][C:12]1[C:3]([CH2:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:15]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 745714-(Chloromethyl)pyridineHCID 5462224MagnesiumHCID 202956342-Bromo-3-ethoxynaphthaleneHCID 178418361HCID 178418361, compound

Product 1

HCID 20295596HCID 20295596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 2.5 g (0.1 mole) of magnesium in 20 ml of tetrahydrofuran is added gradually a solution of 25 g (0.1 mole) of 2-bromo-3-ethoxynaphthalene in 25 ml of tetrahydrofuran. The agitated mixture is refluxed for 1 hour and a solution of 1.4 g (0.1 mole) of 4-chloromethylpyridine dissolved in tetrahydrofuran added gradually. The mixture is refluxed for 3 hours, a saturated ammonium chloride solution is added, the reaction mixture is extracted with ether, and the organic phase washed with sodium carbonate and dried over sodium sulfate. The ether is evaporated and the resulting 4-[(3-ethoxy-2-naphthyl)methyl]pyridine dissolved in acetic acid and agitated in a Parr apparatus in the presence of 1.5 g of platinum oxide. Hydrogen gas is introduced and the reaction continued until 0.3 mole of hydrogen is consumed. The solution is filtered and the solvent removed in vacuo. The residue is dissolved in ether and an excess of dry HCl bubbled through the solution to yield 4 -[(3-ethoxy-2-naphthyl)methyl]piperidine hydrochloride.

Workup

  1. temperatureThe agitated mixture is refluxed for 1 hour
  2. additionadded gradually
  3. temperatureThe mixture is refluxed for 3 hours
  4. extractionthe reaction mixture is extracted with ether
  5. washthe organic phase washed with sodium carbonate
  6. dry with materialdried over sodium sulfate
  7. customThe ether is evaporated
  8. dissolutionthe resulting 4-[(3-ethoxy-2-naphthyl)methyl]pyridine dissolved in acetic acid
  9. additionHydrogen gas is introduced
  10. customis consumed
  11. filtrationThe solution is filtered
  12. customthe solvent removed in vacuo
  13. dissolutionThe residue is dissolved in ether
  14. customan excess of dry HCl bubbled through the solution

Sources & evidence

ORD record
ord-18cdc4523b2048d5a14e93f63c1a5743
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

Loading…