Triethylamine → HCID 67401777, compound

HRID 1186423Notes

Reaction equation

HRID 1186423 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[O:4][Si:5]([CH2:10][CH3:11])([CH2:8][CH3:9])[CH2:6][CH3:7].C(N(CC)CC)C.[C:27](Cl)(=[O:30])[CH2:28][CH3:29].C(=O)(O)[O-].[Na+]>ClCCl>[C:27]([N:15]1[CH2:16][CH2:17][CH:12]([CH:3]([O:4][Si:5]([CH2:8][CH3:9])([CH2:6][CH3:7])[CH2:10][CH3:11])[C:2]([F:18])([F:1])[F:19])[CH2:13][CH2:14]1)(=[O:30])[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 67402546HCID 67402546, compound

Product 1

HCID 67401777HCID 67401777, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[2,2,2-Trifluoro-1-(triethylsiloxy)ethyl]piperidine (250 mg, 0.841 mmol) was dissolved in dichloromethane (5.0 mL). To this, triethylamine (0.176 mL, 1.26 mmol) and propionyl chloride (0.110 mL, 1.26 mmol) were added at 0° C. and the mixture was stirred at room temperature for 2 hours. The reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution to the reaction mixture, and extraction with dichloromethane was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give 1-propionyl-4-[2,2,2-trifluoro-1-(triethylsiloxy)ethyl]-piperidine (231 mg, yield: 78%).

Workup

  1. dry with materialby drying over anhydrous sodium sulfate
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-08cabe95294d4bfea9ddbeb9b4b2bdde
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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