Triethylamine → HCID 86704449, compound

HRID 1754394Notes

Reaction equation

HRID 1754394 reaction equation
[CH2:1]([CH:4]1[NH:8][C:7]([CH3:10])([CH3:9])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C(N(CC)CC)C.[C:18](Cl)(=[O:21])[CH:19]=[CH2:20].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([CH:4]1[N:8]([C:18](=[O:21])[CH:19]=[CH2:20])[C:7]([CH3:10])([CH3:9])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 86704448HCID 86704448, compound

Product 1

HCID 86704449HCID 86704449, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-allyl-2,2-dimethylpyrrolidine (1.5 g, 10.5 mmol) in 50 ml of anhydrous CH2Cl2, triethylamine (3 ml, 21 mmol) and acryloyl chloride (0.94 ml, 11.6 mmol) were added at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and allowed to warm to room temperature and stirred for overnight. Analysis of the reaction mixture by LCMS indicated the completion of the reaction. Saturated aqueous NaHCO3 was added to the reaction mixture and the layers were separated. Aqueous layer was worked up twice with CH2Cl2 and the combined organic layers were dried over Na2SO4. Removal of the volatiles and purification of the crude by column chromatography gave the product in 80% yield (1.60 g) as colorless oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for overnight
  3. customthe completion of the reaction
  4. customthe layers were separated
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. customRemoval of the volatiles and purification of the crude by column chromatography
  7. customgave the product in 80% yield (1.60 g) as colorless oil

Sources & evidence

ORD record
ord-52fd69b5555f47c2a3ce23153dda17e1
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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