Borane → (1-(4-Nitrophenyl)piperidin-4-yl)methanol

HRID 2236833Notes

Reaction equation

HRID 2236833 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16](O)=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].B>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][OH:17])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 27672651-(4-Nitrophenyl)piperidine-4-carboxylic acid

Product 1

HCID 23448266(1-(4-Nitrophenyl)piperidin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 1-(4-nitrophenyl)piperidine-4-carboxylic acid (1.0 g, 4.0 mmol) in tetrahydrofuran (14 mL) is added borane.tetrahydrofuran complex (1.8 M, 7 mL, 13 mmol). After completion of the dropwise addition, the coolant is removed. The mixture is stirred overnight at room temperature and re-cooled to 0° C. in an ice-water bath. Sodium hydroxide solution (1M, 6 mL) is added dropwise. The basic mixture is neutralized by the addition of saturated aqueous ammonium chloride solution. The mixture is extracted 3× with ethyl acetate, and the combined extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give [1-(4-nitro-phenyl)-piperidin-4-yl]-methanol.

Workup

  1. additionAfter completion of the dropwise addition
  2. customthe coolant is removed
  3. temperaturere-cooled to 0° C. in an ice-water bath
  4. additionSodium hydroxide solution (1M, 6 mL) is added dropwise
  5. additionThe basic mixture is neutralized by the addition of saturated aqueous ammonium chloride solution
  6. extractionThe mixture is extracted 3× with ethyl acetate
  7. washthe combined extracts were washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff62a5e5ef6b42a68317195e3869ea76
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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