Trifluoroacetic acid → 2-Isopropyl-4-methoxy-5-piperazin-1-yl-phenol

HRID 2266165Notes

Reaction equation

HRID 2266165 reaction equation
O[C:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:7][C:6]=1[OH:19])([CH3:4])[CH3:3].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH:2]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([N:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[CH:7][C:6]=1[OH:19])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58207872HCID 58207872, compound

Product 1

HCID 595986752-Isopropyl-4-methoxy-5-piperazin-1-yl-phenolYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-(1-Hydroxy-1-methyl-ethyl)4-methoxy-5-piperazin-1-yl-phenol (0.5 g, 1.9 mmol) in dichloromethane under nitrogen at room temperature was aded trifluoroacetic acid (7.2 mL, 93.86 mmol) followed by triethyl silane (3.0 mL, 18.8 mmol). The reaction mixture was stirred for 18 hours at room temperature, and then was evaporated under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous potassium carbonate. The organic layer was separated, washed with water, dried (MgSO4), filtered, and evaporated under reduced pressure to afford 0.47 g (99% ) of 2-Isopropyl-4-methoxy-5-piperazin-1-yl-phenol as an oil.

Workup

  1. customwas evaporated under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated aqueous potassium carbonate
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-389c8b69e57d4effb9f5781dc71ba0d9
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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