1-Benzyl-4-piperidone → HCID 49760211, compound

HRID 1361510Notes

Reaction equation

HRID 1361510 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.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[Mg]Br>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=2[CH3:15])([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 178425073HCID 178425073, compound

Product 1

HCID 49760211HCID 49760211, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Benzyl-4-piperidinone (946 mg, 5 mmol) was added to 5 mL anhydrous THF and cooled to 0° C. under nitrogen. 10 mL of 2,5-dimethylphenylmagnesium bromide (0.5 M solution in THF) was added drop-wise. The reaction was stirred at 0° C. for 10 minutes, then allowed to warm to room temperature and stirred for 1 h. The reaction was concentrated, and brought back up in methanol/H2O/acetic acid (1:1:0.5). The solution was filtered and purified by reverse-phase HPLC (2-99% CH3CN/0.085% TFA) to yield 1-benzyl-4-(2,5-dimethyl-phenyl)-piperidin-4-ol 3a. MS (ESI) m/z (M+H+) 296.2.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 h
  3. concentrationThe reaction was concentrated
  4. filtrationThe solution was filtered
  5. custompurified by reverse-phase HPLC (2-99% CH3CN/0.085% TFA)

Sources & evidence

ORD record
ord-80c8d83f0c154df5ab8244f3ca31da9b
Source dataset
uspto-grants-2011_02
Patent number
US07880007B2

Reaction notes

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