Ammonium Chloride → 1-Methoxypiperidin-4-ol

HRID 2035305Notes

Reaction equation

HRID 2035305 reaction equation
[BH4-].[Na+].[CH3:3][O:4][N:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1.[Cl-].[NH4+]>C(O)C>[CH3:3][O:4][N:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 199366531-Methoxypiperidin-4-one

Product 1

HCID 30226061-Methoxypiperidin-4-olYield 89.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under an atmosphere of argon, 200 ml ethanol was cooled to 10° C. and 3.7 g sodium borohydride was added. A solution of 25 g 1-methoxy-piperidin-4-one (prepared according to J. Org. Chem. 1961, 26, 1867-74) in 200 ml ethanol was added to the stirred suspension, while the temperature was kept in the range of 15-20° C. Then the mixture was stirred at ambient temperature for 3 hours. 50 ml aqueous ammonium chloride was added slowly and then the solvent evaporated. The residue was purified by chromatography on silica gel, using ethyl acetate as a solvent. Thus, 22.8 g 1-methoxy-piperidin-4-ol was obtained.

Workup

  1. customwas kept in the range of 15-20° C
  2. customthe solvent evaporated
  3. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ee4279eae629444bacc75cdd21ca8e1d
Source dataset
uspto-grants-2013_11
Patent number
US08574607B2

Reaction notes

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