Propargyl bromide → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propynyl)piperidine

HRID 26074Notes

Reaction equation

HRID 26074 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[C:12]([OH:22])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]#[CH:32]>C(O)C>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:32][C:31]#[CH:30])[CH2:17]2)=[C:12]([OH:22])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 155715583-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]piperidine

Product 1

HCID 155715593-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1-N-(2-propynyl)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.900 g. (2.97 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]piperidine, 481 mg. (3.49 mmoles) of anhydrous potassium carbonate and 353 mg. (2.97 mmoles) of 1-bromo-2-propyne in 20 ml. of ethanol is heated at reflux for 22 hours. The reaction mixture is then evaporated and dissolved in 100 ml. of saturated sodium bicarbonate and 200 ml. of dichloromethane. The organic extract is washed with two 150 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 100 g. silica gel eluted with 2% methanol-dichloromethane. The product is crystallized from pentane (117 mg., 11.5%).

Workup

  1. additionA mixture of 0.900 g
  2. temperatureat reflux for 22 hours
  3. customThe reaction mixture is then evaporated
  4. dissolutiondissolved in 100 ml
  5. extractionThe organic extract
  6. washis washed with two 150 ml
  7. dry with materialportions of saturated sodium chloride, dried over magnesium sulfate
  8. customevaporated
  9. customThe residue is purified via column chromatography on 100 g
  10. washsilica gel eluted with 2% methanol-dichloromethane
  11. customThe product is crystallized from pentane (117 mg., 11.5%)

Sources & evidence

ORD record
ord-fb985cf35aba424f889843882f4aa87a
Source dataset
uspto-grants-1979_04
Patent number
US04147872

Reaction notes

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