Allyl bromide → N-acetyl-4-allyloxypiperidine

HRID 354840Notes

Reaction equation

HRID 354840 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH2:13](Br)[CH:14]=[CH2:15]>CN(C)C=O.C(O)(C)C.CCOCC>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:15][CH:14]=[CH2:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Product 1

HCID 12920043N-acetyl-4-allyloxypiperidineYield 85%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-acetyl-4-hydroxypiperidine (100 g.) in dimethylformamide (250 ml.) was added dropwise to sodium hydride (38 g., 50% mineral oil dispersion) under an atmosphere of nitrogen. The mixture was stirred for 2 hours then allyl bromide (93 g.) was added slowly whilst maintaining the reaction temperature at 25° C. by external cooling. The mixture was then stirred at room temperature overnight, diluted with isopropanol (20 ml.) and ether (500 ml.), filtered, and evaporated in vacuo. Distillation of the residue gave N-acetyl-4-allyloxypiperidine (108.8 g.), B.P. 128° C./2 mm, identified spectroscopically.

Workup

  1. stirringThe mixture was then stirred at room temperature overnight
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. distillationDistillation of the residue

Sources & evidence

ORD record
ord-3627394d66634e989d272992cc68f01b
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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