1,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrophenoxy)piperidin-1-yl)methyl)phenyl)propan-2-ol → HCID 86670926, compound

HRID 515264Notes

Reaction equation

HRID 515264 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]>CO.[Pd]>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH:19]2[CH2:20][CH2:21][N:16]([CH2:15][C:12]3[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:2]([F:33])([F:1])[F:32])[C:4]([F:5])([F:6])[F:7])=[CH:14][CH:13]=3)[CH2:17][CH2:18]2)=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 866709251,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrophenoxy)piperidin-1-yl)methyl)phenyl)propan-2-ol

Product 1

HCID 86670926HCID 86670926, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1,1,1,3,3,3-Hexafluoro-2-(4-((4-(4-nitrophenoxy)piperidin-1-yl)methyl)phenyl)propan-2-ol (4.01 mmol, 1.92 g) and palladium (10% on carbon, Degussa) (0.040 mmol, 0.085 g) were hydrogenated in methanol (20 mL) at 5 bar for 1 hour at room temperature. The reaction mixture was filtered and the filtrate concentrated under vacuum to afford the title compound. MS (ESI) m/z 449.1 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-b21252ddc4174d2e83a820f12fa6df18
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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