Methanol → 3-(Aminomethyl)-1-benzylpiperidin-4-ol

HRID 657176Notes

Reaction equation

HRID 657176 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH:3]1[C:15]([NH2:17])=O.B.CSC.CO>C1COCC1>[NH2:17][CH2:15][CH:3]1[CH:2]([OH:1])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 68684193HCID 68684193, compound

Product 1

HCID 230037323-(Aminomethyl)-1-benzylpiperidin-4-olYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-hydroxy-1-(phenylmethyl)-3-piperidinecarboxamide (5.62 g, 23.9 mmol) in THF (65 mL) was treated dropwise with borane-methyl sulphide complex (2M solution in THF, 26.4 mL, 52.8 mmol). After stirring for 0.5 h at room temperature, the reaction mixture was heated at 80° C. for 1.5 h. Methanol (16 mL) was added and heating continued for 0.5 h. The mixture was evaporated and the residue was chromatographed on silica gel, eluting with 10-30% (2M ammonia/methanol)/dichloromethane to give the product (2.67 g, 51%).

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 1.5 h
  2. temperatureheating
  3. waitcontinued for 0.5 h
  4. customThe mixture was evaporated
  5. customthe residue was chromatographed on silica gel
  6. washeluting with 10-30% (2M ammonia/methanol)/dichloromethane

Sources & evidence

ORD record
ord-2a805150c29f4d3598fcd09386911c3a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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