Iodine → HCID 20295617, compound

HRID 1389866Notes

Reaction equation

HRID 1389866 reaction equation
[Mg].II.[F:4][C:5]([F:18])([F:17])[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8](Br)[CH:7]=1.[N:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=1.[Cl-:27].[NH4+].[H][H]>O1CCCC1>[ClH:27].[F:4][C:5]([F:18])([F:17])[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([CH:25]([CH:22]2[CH2:23][CH2:24][NH:19][CH2:20][CH2:21]2)[OH:26])[CH:7]=1

Participants

8

Reactant 6

HCID 807IodineHCID 133894-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 20295540HCID 20295540, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20295617HCID 20295617, 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 a crystal of iodine and a solution of 27.5 g (0.1 mole) of 1-trifluoromethyl-3-bromonaphthalene in 25 ml of tetrahydrofuran. The agitated mixture is refluxed for 1 hour, whereupon 10.7 g (0.1 mole) of 4-pyridinecarboxaldehyde dissolved in 50 ml of tetrahydrofuran is added gradually and heating continued for 3 hours. The reaction mixture is decomposed with saturated aqueous ammonium chloride solution and extracted with ether and the organic phase washed with sodium carbonate, dried over NaSO4 and filtered. The ether is evaporated and the resulting α-(4-trifluoromethyl-2-naphthyl)-4-pyridinemethanol dissolved in 150 ml of 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 moles of hydrogen are consumed. The mixture is filtered and the solvent removed in vacuo. Addition to the residue of an excess of HCl in ethereal solution yields α(4-trifluoromethyl-2-naphthyl)-4-piperidinemethanol hydrochloride.

Workup

  1. additionis added gradually
  2. temperatureheating
  3. extractionextracted with ether
  4. washthe organic phase washed with sodium carbonate
  5. dry with materialdried over NaSO4
  6. filtrationfiltered
  7. customThe ether is evaporated
  8. dissolutionthe resulting α-(4-trifluoromethyl-2-naphthyl)-4-pyridinemethanol dissolved in 150 ml of acetic acid
  9. additionHydrogen gas is introduced
  10. customare consumed
  11. filtrationThe mixture is filtered
  12. customthe solvent removed in vacuo
  13. additionAddition to the residue of an excess of HCl in ethereal solution

Sources & evidence

ORD record
ord-0922ea428b234d9d8e1b85c1a27ce081
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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