1-Benzyl-4-hydroxypiperidine-4-carbonitrile → 4-(Aminomethyl)-1-benzylpiperidin-4-ol

HRID 1827149Notes

Reaction equation

HRID 1827149 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:16])([C:14]#[N:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>>[NH2:15][CH2:14][C:11]1([OH:16])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 801891-Benzyl-4-hydroxypiperidine-4-carbonitrileHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 104210264-(Aminomethyl)-1-benzylpiperidin-4-ol

Conditions

Temperature
80 °C

Procedure

A mixture of 1-benzyl-4-hydroxy-piperidine-4-carbonitrile (5.00 g, 19.78 mmol) and BH3.THF (59.35 mmol, 59.35 mL, 1M in THF) was heated at 80° C. for 1 h. Cooled to 0° C. and quenched with conc. HCl (20 mL), the reaction solution was then stirred at rt in 1 h. The reaction solution was basified with 10N NaOH to pH8, and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (50 mL), brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo to give 4-aminomethyl-1-benzyl-piperidin-4-ol. M.S.(M+1):221.31

Workup

  1. temperatureCooled to 0° C.
  2. customquenched with conc. HCl (20 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined extracts were washed with water (50 mL), brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-285d5f9b9e8f4c6282a8ebac4808dbbb
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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