4-Methylbenzyl alcohol → HCID 57845343, compound

HRID 734381Notes

Reaction equation

HRID 734381 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]([N:17]1[CH:21]=[CH:20]N=[CH:18]1)(N1C=CN=C1)=[O:11].Cl.O.N1CC[C:27](=[O:30])[CH2:26]C1>CN(C=O)C.CCOC(C)=O>[O:30]=[C:27]1[CH2:26][CH2:18][N:17]([C:10]([O:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:11])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 115054-Methylbenzyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 2723901Piperonylamine

Product 1

HCID 57845343HCID 57845343, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

4-Methylbenzyl alcohol (37.6 g, 308 mmol) was added to a solution of 1,1′-carbonyldiimidazole (50.0 g, 308 mmol) in DMF at RT and stirred for 1 h. 4-Piperidone hydrate hydrochloride (commercially available from Sigma-Aldrich, 47.0 g, 308 mmol) was added, resulting in a reaction mixture that was then heated to 50° C. and stirred for 15 h. The reaction mixture was diluted with EtOAc and washed with 0.1 M HCl, H2O (four times), and brine, dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (step gradient elution: 10%, 25%, 50% EtOAc in hexanes) produced the title compound (42.4 g, 85% yield) as a clear oil.

Workup

  1. customresulting in a reaction mixture that
  2. stirringstirred for 15 h
  3. washwashed with 0.1 M HCl, H2O (four times), and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. washby silica gel chromatography (step gradient elution: 10%, 25%, 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-808c0e6b4de84568a1cebdb2178894a2
Source dataset
uspto-grants-2009_09
Patent number
US07592360B2

Reaction notes

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