Propargyl bromide → 1-(Prop-2-yn-1-yl)piperidin-2-one

HRID 2296013Notes

Reaction equation

HRID 2296013 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].[CH2:10](Br)[C:11]#[CH:12]>CCCCCC.C1(C)C=CC=CC=1>[CH2:12]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9])[C:11]#[CH:10]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 126652-PiperidoneHCID 24758Sodium hydride2×

Product 1

HCID 132897941-(Prop-2-yn-1-yl)piperidin-2-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
15 °C

Procedure

Sodium hydride (5.76 g of 50% dispersion in oil, 0.12 mole) was washed three times with hexane and suspended in 645 ml of toluene. 2-Piperidone (11.88 g, 0.12 mole) in 100 ml of toluene was added to the well stirred sodium hydride suspension and heated to reflux for 2 hours. The reaction mixture was cooled to 15° C. and 2-propynyl bromide (14.28 g, 0.12 mole) in 55 ml of toluene added over 30 minutes. The mixture was then stirred at room temperature for 19 hours, filtered and mother liquor evaporated to yield a first batch of 1-(2-propynyl)-2-piperidone as an oil (7.87 g of about 55% purity by pnmr assay).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered
  4. custommother liquor evaporated

Sources & evidence

ORD record
ord-d4d90c506337401c81f2eb2abdb85b3d
Source dataset
uspto-grants-1984_01
Patent number
US04427679

Reaction notes

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