Dimethylformamide → 1-Acetyl-3-benzyloxypiperidine

HRID 355124Notes

Reaction equation

HRID 355124 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([OH:10])[CH2:5]1)(=[O:3])[CH3:2].CN(C)C=O.[H-].[Na+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([O:10][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 218970301-(3-Hydroxypiperidin-1-yl)ethan-1-one

Product 1

HCID 205061191-Acetyl-3-benzyloxypiperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Acetyl-3-hydroxypiperidine (0.10 mole) is dissolved in 50 ml. of dimethylformamide. 0.12 Mole of sodium hydride (56%) is added over a 10 minute period, and the reaction mixture is stirred for 30 minutes. Benzyl chloride (0.12 mole) is added dropwise over a 30 minute period, and the reaction mixture is then heated on a steam bath for 30 minutes. Water (3 volumes) is added, the solution extracted with ether, the ether extract washed with water and the ether removed by evaporation. A yellow oil is obtained on distillation at 136°-140° C. (0.01 mm Hg.).

Workup

  1. temperaturethe reaction mixture is then heated on a steam bath for 30 minutes
  2. extractionthe solution extracted with ether
  3. extractionthe ether extract
  4. washwashed with water
  5. customthe ether removed by evaporation
  6. customA yellow oil is obtained on distillation at 136°-140° C. (0.01 mm Hg.)

Sources & evidence

ORD record
ord-290ac57bed404a7dac0e126a88c6a994
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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