Water → 1-Benzyl-4-isopropylpiperidin-4-ol

HRID 734784Notes

Reaction equation

HRID 734784 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.[CH:15]([Mg]Cl)([CH3:17])[CH3:16].O.CCOC(C)=O>C1COCC1.C(OCC)C.C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH:15]([CH3:17])[CH3:16])([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 192201-Benzyl-4-piperidoneHCID 178418918HCID 178418918, compound

Product 1

HCID 690614431-Benzyl-4-isopropylpiperidin-4-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21868444Ether tetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, first 700 mL of a THF/diethyl ether mixture (2:1) and then a solution of 53.0 mL (283 mmol) of N-benzyl-4-piperidone in 200 mL of a THF/diethyl ether mixture (2:1) were slowly added at −15° C. to 200 mL (400 mmol, 2 M in THF) of isopropylmagnesium chloride solution and the reaction mixture was stirred for 1 hour between −3° C. and −6° C. While cooling with ice, 600 mL of water was slowly added dropwise and the mixture was stirred for 30 minutes. Then 400 mL of EtOAc and 100 mL of diethyl ether were added. The organic phase was separated off and dried over sodium sulfate. After the desiccant and solvent had been eliminated, the residue was purified by chromatography (silica gel, DCM/MeOH/NH3 98:2:0.2). Yield: 9.85 g (15% of theoretical); C15H23NO (M=233.349); calc.: molpeak (M+H)+: 234; found: molpeak (M+H)+: 234; HPLC-MS: 4.1 minutes (method G).

Workup

  1. additionwas slowly added dropwise
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe organic phase was separated off
  4. dry with materialdried over sodium sulfate
  5. customthe residue was purified by chromatography (silica gel, DCM/MeOH/NH3 98:2:0.2)
  6. custom4.1 minutes (method G)

Sources & evidence

ORD record
ord-52c34e08a868420597380295170c37e6
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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