Propargyl bromide → HCID 22147965, compound

HRID 1823893Notes

Reaction equation

HRID 1823893 reaction equation
[F:1][C:2]([F:10])([F:9])[CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH2:11](Br)[C:12]#[CH:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:13]([N:6]1[CH2:7][CH2:8][CH:3]([C:2]([F:10])([F:9])[F:1])[CH2:4][CH2:5]1)[C:12]#[CH:11]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 1364694-(Trifluoromethyl)piperidine

Product 1

HCID 22147965HCID 22147965, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Trifluoromethylpiperidine (2.0 g, 13 mmol) was added to a solution of propargyl bromide (80 wt. % 5.4 g, 36 mmol) in ethanol (30 ml). Potassium carbonate (5.4 g, 39 mmol) was added and the mixture was stirred at room temperature for 20 hours. The mixture was filtered and the solids washed with ethyl acetate. The filtrate was evaporated in vacuo, diluted with sodium hydrogen carbonate (sat, 50 ml) and extracted with ethyl acetate (2×40 ml). The extracts were washed with brine, dried (MgSO4) and evaporated in vacuo to provide 1-propargyl-4-trifluoromethylpiperidine as a brown oil (795 mg, 32%). (ES+) 192 ([MH]+).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids washed with ethyl acetate
  3. customThe filtrate was evaporated in vacuo
  4. additiondiluted with sodium hydrogen carbonate (sat, 50 ml)
  5. extractionextracted with ethyl acetate (2×40 ml)
  6. washThe extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-e6c71a726c8a4e29b5a6f094b58c8906
Source dataset
uspto-grants-2006_05
Patent number
US07041688B2

Reaction notes

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