Propargyl bromide → HCID 15571563, compound

HRID 444349Notes

Reaction equation

HRID 444349 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][NH:18][CH2:19][CH2:20][CH:21]=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]([C:16]2[CH2:17][N:18]([CH2:32][C:31]#[CH:30])[CH2:19][CH2:20][CH:21]=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 155715613-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine

Product 1

HCID 15571563HCID 15571563, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.0 g. (3.33 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine, 539 mg. (3.90 mmoles) of anhydrous potassium carbonate and 395 mg. (3.32 mmoles) of 1-bromo-2-propyne in 23 ml. of ethanol is heated at reflux for 20 hours. The reaction mixture is 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 crystallized from pentane to yield 161 mg. of the title compound.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureat reflux for 20 hours
  3. customThe reaction mixture is 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 crystallized from pentane
  10. customto yield 161 mg

Sources & evidence

ORD record
ord-d260e29aa9694034b9fb23a536f09e12
Source dataset
uspto-grants-1981_04
Patent number
US04263438

Reaction notes

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