Trifluoroacetic acid → 1-(4-{[4-(Propan-2-yloxy)phenoxy]methyl}benzyl)piperazine

HRID 1023349Notes

Reaction equation

HRID 1023349 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:32]=[CH:31][C:8]([O:9][CH2:10][C:11]2[CH:30]=[CH:29][C:14]([CH2:15][N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:3].C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:3][CH:2]([O:4][C:5]1[CH:32]=[CH:31][C:8]([O:9][CH2:10][C:11]2[CH:30]=[CH:29][C:14]([CH2:15][N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67328500Tert-butyl 4-(4-{[4-(propan-2-yloxy)phenoxy]methyl}benzyl)piperazine-1-carboxylate

Product 1

HCID 673276971-(4-{[4-(Propan-2-yloxy)phenoxy]methyl}benzyl)piperazineYield 136.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-{[4-(propan-2-yloxy)phenoxy]methyl}benzyl)-piperazine-1-carboxylate (5.42 g) in CH2Cl2 (41 mL) was added TFA (10 mL) at room temperature, then the reaction mixture was stirred for 8 hours. The reaction mixture was basified with 5 M aqueous NaOH, and extracted with CH2Cl2. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 1-(4-{[4-(propan-2-yloxy)phenoxy]methyl}benzyl)piperazine as a colorless solid (5.73 g).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with water and saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dbde279ecdb747d1a9b879cd89001f0f
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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