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

HRID 81836Notes

Reaction equation

HRID 81836 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 added 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-415c03af31ec4134b6a223d377c0bed2
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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