Trifluoroacetic acid → 1,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

HRID 1807765Notes

Reaction equation

HRID 1807765 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].FC(F)(F)C(O)=O>ClCCl>[F:29][C:2]([F:1])([F:30])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:27][CH:28]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59175874tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carboxylate

Product 1

HCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-olYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carboxylate (16.09 mmol, 7.12 g) in dichloromethane (30 mL) was added trifluoroacetic acid (5 mL) and the reaction stirred at room temperature for 2 hours. The reaction mixture was concentrated under vacuum and purified by SCX chromatography to afford the title compound (3.5 g). MS (ESI) m/z 343.1 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by SCX chromatography

Sources & evidence

ORD record
ord-0a70e9e6ae6745c7852856b7b18e2f9a
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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