Trifluoroacetic acid → 1,1,1,3,3,3-Hexafluoro-2-(4-((4-(methylamino)piperidin-1-yl)methyl)phenyl)propan-2-ol

HRID 515326Notes

Reaction equation

HRID 515326 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20](C)[C:21](=O)OC(C)(C)C)[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:32][C:2]([F:1])([F:31])[C:3]([C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([NH:20][CH3:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86670960Tert-butyl 1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-piperidin-4-yl(methyl)carbamate

Product 1

HCID 866709591,1,1,3,3,3-Hexafluoro-2-(4-((4-(methylamino)piperidin-1-yl)methyl)phenyl)propan-2-olYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-piperidin-4-yl(methyl)carbamate (3.19 mmol, 1.5 g), dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was stirred for 20 hours. Purification by SCX chromatography gave the title compound (1.1 g). MS (ESI) m/z 371.4 [M+H]+

Workup

  1. customPurification by SCX chromatography

Sources & evidence

ORD record
ord-36a46946967e4f99b3a397206ae6540f
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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