1-Benzyl-4-piperidone → 4-(Aminomethyl)-1-benzylpiperidin-4-ol

HRID 565607Notes

Reaction equation

HRID 565607 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:19]#[N:20])(C)C>C(OCC)C.[I-].[Zn+2].[I-]>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:14])([CH2:19][NH2:20])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 82115Trimethylsilyl cyanide

Product 1

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

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To neat 1-benzyl-4-piperidone (2.22 mL, 12 mmol) was added trimethylsilyl cyanide (1.95 mL, ˜15 mmol) and zinc iodide (˜5 mg). The solution was stirred for 6 hours or until reaction was completed as indicated by tlc. This oil was dissolved in diethyl ether (30 mL), filtered to remove some solid and added dropwise to a solution of diethyl ether (15 mL) containing 1M lithium aluminium hydride/diethyl ether (30 mL). After stirring at ambient temp. for 2 hours, the reaction was carefully quenched with aqueous sat'd sodium sulfate. This suspension was diluted with more diethyl ether, filtered to remove solids, and the solvent evaporated under partial vacuum to give the crude title compound as an oil.

Workup

  1. filtrationfiltered
  2. customto remove some solid
  3. additionadded dropwise to a solution of diethyl ether (15 mL)
  4. additioncontaining 1M lithium aluminium hydride/diethyl ether (30 mL)
  5. stirringAfter stirring at ambient temp. for 2 hours
  6. customthe reaction was carefully quenched with aqueous sat'd sodium sulfate
  7. additionThis suspension was diluted with more diethyl ether
  8. filtrationfiltered
  9. customto remove solids
  10. customthe solvent evaporated under partial vacuum

Sources & evidence

ORD record
ord-e2ced07f05bf48b1a891fb5edf94ac43
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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