Sodium Bicarbonate → 5-Hydroxy-1-methyl-3-(4-methylphenyl)-1,2,5,6-tetrahydropyridine

HRID 2166572Notes

Reaction equation

HRID 2166572 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][N:13]([CH3:15])[CH2:12][C:11](=[O:16])[CH:10]=2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>C(O)C>[OH:16][CH:11]1[CH2:12][N:13]([CH3:15])[CH2:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH3:2])=[CH:8][CH:7]=2)=[CH:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 204998081,6-dihydro-5-(4-methylphenyl)-1-methyl-3[2H]pyridone hydrochloride

Product 1

HCID 129007105-Hydroxy-1-methyl-3-(4-methylphenyl)-1,2,5,6-tetrahydropyridineYield 58.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,6-dihydro-5-(4-methylphenyl)-1-methyl-3[2H]pyridone hydrochloride (18 g) in 50% aqueous ethanol (500 ml) was treated with sodium bicarbonate (6.4 g) followed by sodium borohydride (4 g) in portions. After 2 hours, the solvent was removed under reduced pressure and the residue extracted with ether (2×250 ml). Drying (MgSO4) followed by removal of the solvent under vacuum gave an oil which crystallised and was recrystallised from pentane to give the title compound (9 g) m.p. 67°-69°.

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionthe residue extracted with ether (2×250 ml)
  3. dry with materialDrying (MgSO4)
  4. customfollowed by removal of the solvent under vacuum
  5. customgave an oil which
  6. customcrystallised
  7. customwas recrystallised from pentane

Sources & evidence

ORD record
ord-ee2d21ca19fd48eea45e700aed92b335
Source dataset
uspto-grants-1983_06
Patent number
US04387230

Reaction notes

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