Trifluoroacetic acid → HCID 71542292, compound

HRID 629541Notes

Reaction equation

HRID 629541 reaction equation
[C:1]12([C:11]3[CH:33]=[CH:32][C:14]([O:15][CH2:16][C:17]([N:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.FC(F)(F)C(O)=O>ClCCl>[C:1]12([C:11]3[CH:33]=[CH:32][C:14]([O:15][CH2:16][C:17]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71542291HCID 71542291, compound

Product 1

HCID 71542292HCID 71542292, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-(4-(adamantan-1-yl)phenoxy)acetyl)piperazine-1-carboxylate (0.15 g, 0.42 mmol), prepared from the example 29, in dichloromethane (1.5 mL) was added trifluoroacetic acid (0.15 g, 1.69 mmol) and stirred at room temperature overnight. The reaction mixture was concentrated and diluted with dichloromethane. The organic layer was washed with aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by silica gel column chromatography to give 2-(4-(adamantan-1-yl)phenoxy)-1-(piperazin-1-yl)ethanone as a white solid (0.11 g, 94.8% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with dichloromethane
  3. washThe organic layer was washed with aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solvent was filtered
  6. customevaporated under reduced pressure
  7. customto afford a crude solid, which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4b78dd02568d4cdc939042cfcfaf88a3
Source dataset
uspto-grants-2016_04
Patent number
US09315507B2

Reaction notes

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