Sodium borohydride → 4-(4-Hydroxypiperidin-1-yl)benzonitrile

HRID 1264325Notes

Reaction equation

HRID 1264325 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[BH4-].[Na+]>CO.O>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 110198874-(4-Oxopiperidin-1-yl)benzonitrile

Product 1

HCID 111064164-(4-Hydroxypiperidin-1-yl)benzonitrileYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

240 mg (1.2 mmol) of 4-(4-oxo-piperidin-1-yl)-benzonitrile (reference example 116) was dissolved in 5 ml of methanol, 23 mg (0.6 mmol) of NaBH4 was added and stirred 3 h at room temperature. A few drops of water were added, methanol evaporated then 20 ml of water were added and extracted with DCM (3×), dried with Na2SO4, filtered and evaporated to give 230 mg (95% yield) of the title compound. 1H NMR (CDCl3): d 7.47 (d, 2H), 6.85 (d, 2H), 3.93 (bs, H), 3.70 (m, 2H), 3.11 (m, 2H), 1.95 (m, 2H), 1.62 (m, 2H). MS (ion spray) m/z 202 (M+H)+.

Workup

  1. custommethanol evaporated
  2. addition20 ml of water were added
  3. extractionextracted with DCM (3×)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-85baffa914a34581b3df0fc312dce097
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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