Trifluoroacetic acid → HCID 86692520, compound

HRID 1748575Notes

Reaction equation

HRID 1748575 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([Br:22])=[CH:17][N:16]=2)=[CH:11][CH2:10]1)C)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[Br:22][C:18]1[CH:19]=[C:20]([CH3:21])[C:15]([C:12]2[CH2:13][CH2:14][CH:9]([NH:7][CH3:6])[CH2:10][CH:11]=2)=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86692517HCID 86692517, compound

Product 1

HCID 86692520HCID 86692520, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]-N-methylcarbamic acid tert-butyl ester (11.6 g) described in Reference Example 143 (5) in dichloromethane (30 ml) was added trifluoroacetic acid (10 ml) at room temperature, and stirred at 50° C. for 4 hours. After completion of the reaction, a saturated aqueous solution of sodium hydrogen carbonate was added thereto under ice-cooling, and extracted with 10% methanol/chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with basic silica gel column chromatography (chloroform) to give N-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]-N-methylamine (8.13 g) as a brown oil.

Workup

  1. customAfter completion of the reaction
  2. temperatureunder ice-cooling
  3. extractionextracted with 10% methanol/chloroform
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified with basic silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-bd44ff75996f48deb89bcb767a8e5df5
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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