Hydrochloric Acid → 3-(3-Methoxyphenyl)piperidine hydrochloride

HRID 2108194Notes

Reaction equation

HRID 2108194 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7]OC2C=CC=CC=2)[CH:2]=1.[ClH:15].[CH3:16][OH:17]>O=[Pt]=O>[ClH:15].[CH3:16][O:17][C:3]1[CH:2]=[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][NH:1][CH2:2]2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 124744313-(Phenoxymethyl)pyridine

Product 1

HCID 199872553-(3-Methoxyphenyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

To a solution of 3-(3-pyridinyl)methoxybenzene (22.0 g, 0.099 mol) in methanol (250 ml), PtO2 (2 g) and conc. HCl (30 ml) were added and the mixture was hydrogenated at 0.34 MPa in a Parr apparatus. After complete hydrogenation, the catalyst was filtered off Most of the solvent was evaporated, the residue was made alkaline with 1M NaOH and extracted with ether. The ether-phase was dried (Na2SO4) and the solvent evaporated giving 18 g of the amine product. The hydrochloride was made and then recrystallized from ethanol/ether yielding 20.9 g (93%), mp. 137-138.5° C.

Workup

  1. filtrationAfter complete hydrogenation, the catalyst was filtered off Most of the solvent
  2. customwas evaporated
  3. extractionextracted with ether
  4. dry with materialThe ether-phase was dried (Na2SO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-190a2a928088492197e067a8915bba0f
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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