Sodium borohydride → 1-Benzyl-4-methyl-1,2,3,6-tetrahydropyridine

HRID 2122039Notes

Reaction equation

HRID 2122039 reaction equation
[Cl-].[CH2:2]([N+:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C.O>[CH2:2]([N:9]1[CH2:10][CH:11]=[C:12]([CH3:15])[CH2:13][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10856996Pyridinium, 4-methyl-1-(phenylmethyl)-, chloride (1:1)

Product 1

HCID 64215721-Benzyl-4-methyl-1,2,3,6-tetrahydropyridineYield 100%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of the product from Method A (38 grams/0.171 mol) dissolved in 140 mL of 10:1 ethanol/water at 0° C. was added 16 grams (0.427 mol) of sodium borohydride portion-wise over 25 minutes. The resulting mixture stirred for 18 hours at room temperature, at which time, the reaction was quenched upon addition of 100 mL of water. The reaction mixture was filtered, the filter cake washed with water and ethylacetate, and the combined filtrates concentrated under reduced pressure to remove the organics. The residue was diluted with water (100 mL) and extracted 3 times with 150 mL with ethylacetate. The combined ethylacetate extracts were dried over Na2SO4 and concentrated to dryness in vacuo affording 32 grams (100%) of the title compound as a yellow oil. LRMS: 188 (M+1).

Workup

  1. customthe reaction was quenched upon addition of 100 mL of water
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake washed with water and ethylacetate
  4. concentrationthe combined filtrates concentrated under reduced pressure
  5. customto remove the organics
  6. additionThe residue was diluted with water (100 mL)
  7. extractionextracted 3 times with 150 mL with ethylacetate
  8. dry with materialThe combined ethylacetate extracts were dried over Na2SO4
  9. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-127692d30b9844b88dc66002125de2f2
Source dataset
uspto-grants-2004_02
Patent number
US06696567B2

Reaction notes

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